JPH0341456B2 - - Google Patents

Info

Publication number: JPH0341456B2
Authority: JP; Japan
Prior art keywords: methoxy; naphthyl; general formula; compound; reaction
Prior art date: 1988-07-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP18017288A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6470431A (en

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-07-21

Filing date

1988-07-21

Publication date

1991-06-24

1988-07-21 Application filed filed Critical

1988-07-21 Priority to JP18017288A priority Critical patent/JPS6470431A/ja

1989-03-15 Publication of JPS6470431A publication Critical patent/JPS6470431A/ja

1991-06-24 Publication of JPH0341456B2 publication Critical patent/JPH0341456B2/ja

Status Granted legal-status Critical Current

Links

DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
150000001875 compounds Chemical class 0.000 description 25
238000000034 method Methods 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
-1 Trans-6-methoxy-2-(1-propenyl)naphthalene Chemical compound 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
150000001241 acetals Chemical class 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000005694 sulfonylation reaction Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 3
GIFLQCVVIWXBBS-UHFFFAOYSA-N 1,1-dimethoxy-1-(6-methoxynaphthalen-2-yl)propan-2-ol Chemical compound C1=C(C(OC)(OC)C(C)O)C=CC2=CC(OC)=CC=C21 GIFLQCVVIWXBBS-UHFFFAOYSA-N 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
238000005727 Friedel-Crafts reaction Methods 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
XFSFCYMBIFIDHI-UHFFFAOYSA-N [1,1-dimethoxy-1-(6-methoxynaphthalen-2-yl)propan-2-yl] methanesulfonate Chemical compound C1=C(C(OC)(OC)C(C)OS(C)(=O)=O)C=CC2=CC(OC)=CC=C21 XFSFCYMBIFIDHI-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
ZFYFBPCRUQZGJE-UHFFFAOYSA-N methyl 2-(6-methoxynaphthalen-2-yl)propanoate Chemical compound C1=C(OC)C=CC2=CC(C(C)C(=O)OC)=CC=C21 ZFYFBPCRUQZGJE-UHFFFAOYSA-N 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
NSBNSZAXNUGWDJ-UHFFFAOYSA-O monopyridin-1-ium tribromide Chemical compound Br[Br-]Br.C1=CC=[NH+]C=C1 NSBNSZAXNUGWDJ-UHFFFAOYSA-O 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
FYWSTUCDSVYLPV-UHFFFAOYSA-N nitrooxythallium Chemical compound [Tl+].[O-][N+]([O-])=O FYWSTUCDSVYLPV-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
PHJFLPMVEFKEPL-UHFFFAOYSA-N (6-methoxy-2-naphthyl)acetic acid Chemical compound C1=C(CC(O)=O)C=CC2=CC(OC)=CC=C21 PHJFLPMVEFKEPL-UHFFFAOYSA-N 0.000 description 1
UIOXNNAWANDJCZ-UHFFFAOYSA-N 1,1-dimethoxypropane Chemical compound CCC(OC)OC UIOXNNAWANDJCZ-UHFFFAOYSA-N 0.000 description 1
238000007148 1,2 rearrangement reaction Methods 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
GGWCZBGAIGGTDA-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)ethanone Chemical compound C1=C(C(C)=O)C=CC2=CC(OC)=CC=C21 GGWCZBGAIGGTDA-UHFFFAOYSA-N 0.000 description 1
LWOTXBQKJLOAOZ-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)propan-1-one Chemical compound C1=C(OC)C=CC2=CC(C(=O)CC)=CC=C21 LWOTXBQKJLOAOZ-UHFFFAOYSA-N 0.000 description 1
RCGQAPUWWHXBOK-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)propanal Chemical compound C1=C(C(C)C=O)C=CC2=CC(OC)=CC=C21 RCGQAPUWWHXBOK-UHFFFAOYSA-N 0.000 description 1
XCOAABZEUNQHQG-UHFFFAOYSA-N 2-bromo-1-(6-methoxynaphthalen-2-yl)propan-1-one Chemical compound C1=C(C(=O)C(C)Br)C=CC2=CC(OC)=CC=C21 XCOAABZEUNQHQG-UHFFFAOYSA-N 0.000 description 1
AYFJBMBVXWNYLT-UHFFFAOYSA-N 2-bromo-6-methoxynaphthalene Chemical compound C1=C(Br)C=CC2=CC(OC)=CC=C21 AYFJBMBVXWNYLT-UHFFFAOYSA-N 0.000 description 1
BJRXZMCJFCAZDL-UHFFFAOYSA-N 2-bromopropanal Chemical compound CC(Br)C=O BJRXZMCJFCAZDL-UHFFFAOYSA-N 0.000 description 1
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
VKCNNDPZFOVURD-UHFFFAOYSA-N 2-naphthalen-1-ylpropanoic acid Chemical compound C1=CC=C2C(C(C(O)=O)C)=CC=CC2=C1 VKCNNDPZFOVURD-UHFFFAOYSA-N 0.000 description 1
KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
238000005659 Kindler reaction Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 description 1
BGABKEVTHIJBIW-GMSGAONNSA-N [(1r,4s)-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonyl chloride Chemical compound C1C[C@@]2(CS(Cl)(=O)=O)C(=O)C[C@@H]1C2(C)C BGABKEVTHIJBIW-GMSGAONNSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
WEDIIKBPDQQQJU-UHFFFAOYSA-N butane-1-sulfonyl chloride Chemical compound CCCCS(Cl)(=O)=O WEDIIKBPDQQQJU-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000005283 haloketone group Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP18017288A 1988-07-21 1988-07-21 1-(6-methoxy-2-naphthyl)-2-oxy-1-alkanone acetal Granted JPS6470431A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP18017288A JPS6470431A (en)	1988-07-21	1988-07-21	1-(6-methoxy-2-naphthyl)-2-oxy-1-alkanone acetal

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP18017288A JPS6470431A (en)	1988-07-21	1988-07-21	1-(6-methoxy-2-naphthyl)-2-oxy-1-alkanone acetal

Publications (2)

Publication Number	Publication Date
JPS6470431A JPS6470431A (en)	1989-03-15
JPH0341456B2 true JPH0341456B2 (fi)	1991-06-24

Family

ID=16078654

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP18017288A Granted JPS6470431A (en)	1988-07-21	1988-07-21	1-(6-methoxy-2-naphthyl)-2-oxy-1-alkanone acetal

Country Status (1)

Country	Link
JP (1)	JPS6470431A (fi)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP3395806B1 (en)	2017-04-24	2020-04-08	IGM Group B.V.	Simple oxidative functionalization of alkyl aryl ketones

1988
- 1988-07-21 JP JP18017288A patent/JPS6470431A/ja active Granted

Also Published As

Publication number	Publication date
JPS6470431A (en)	1989-03-15

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US4539420A (en)	1985-09-03	Optically active 1-aromatic-group-substituted-1-alkanones and methods for their manufacture
EP0048136B1 (en)	1986-06-11	Process for preparing alpha-aromatic group substituted alkanoic acids or esters thereof
SU1075972A3 (ru)	1984-02-23	Способ получени производных @ -дигалоидвинилциклопропана
JPH0341456B2 (fi)	1991-06-24
Yamauchi et al.	1987	Preparation of methyl 2-arylpropanoates by the reaction of 2-hydroxypropiophenone dimethyl acetals with sulfuryl chloride in the presence of an amide or a weak base.
EP0037697B1 (en)	1984-08-01	Dioxolane derivatives for use as chemical intermediates
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FI80028C (fi)	1990-04-10	Foerfarande foer framstaellning av alfa- substituerade alkylarylketaler.
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JPS6051463B2 (ja)	1985-11-14	（２−フルオロ−４−ビフェニリル）ケテンメルカプタ−ルｓ−オキシド類
JPH08253472A (ja)	1996-10-01	ジベンゾチエピン誘導体の製造方法
JP2581186B2 (ja)	1997-02-12	４−置換−２−シクロペンテノンエステル誘導体の製造法
JPH0246018B2 (fi)	1990-10-12