GB791953A - Novel cyclic diketones and ketals thereof and a process for the manufacture of the same - Google Patents

Novel cyclic diketones and ketals thereof and a process for the manufacture of the same

Info

Publication number
GB791953A
GB791953A GB2098756A GB2098756A GB791953A GB 791953 A GB791953 A GB 791953A GB 2098756 A GB2098756 A GB 2098756A GB 2098756 A GB2098756 A GB 2098756A GB 791953 A GB791953 A GB 791953A
Authority
GB
United Kingdom
Prior art keywords
trimethyl
cyclohexen
ketals
prepared
diketones
Prior art date
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
GB2098756A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Priority to GB2098756A priority Critical patent/GB791953A/en
Publication of GB791953A publication Critical patent/GB791953A/en
Expired legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41L—APPARATUS OR DEVICES FOR MANIFOLDING, DUPLICATING OR PRINTING FOR OFFICE OR OTHER COMMERCIAL PURPOSES; ADDRESSING MACHINES OR LIKE SERIES-PRINTING MACHINES
    • B41L1/00—Devices for performing operations in connection with manifolding by means of pressure-sensitive layers or intermediaries, e.g. carbons; Accessories for manifolding purposes
    • B41L1/20—Manifolding assemblies, e.g. book-like assemblies
    • B41L1/22—Manifolding assemblies, e.g. book-like assemblies made up of single sheets or forms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/603—Unsaturated compounds containing a keto groups being part of a ring of a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises cyclic diketones of formula <FORM:0791953/IV (b)/1> wherein the broken line indicates that a double bond may be present in the 2,3-position, and 4 : 4-ketals thereof, such as 2 : 6 : 6-trimethyl4 : 4 - ethylenedioxy - cyclohexen - (2) - one and 2 : 6 : 6 - trimethyl - 4 : 4 - ethylenedioxy - cyclohexanone. The diketones and ketals are prepared by oxidizing 2 : 6 : 6 - trimethyl - cyclohexen - (2) - ol - (1) - one - (4) (cf. Specification 791,954) to give 2 : 6 : 6-trimethyl-cyclohexen-(2)-dione-(1 : 4) and, if desired, hydrogenating the nuclear double bond and/or ketalizing the 4-oxo group. The oxidation may be carried out in known manner using, e.g. chromic acid or tertiary butyl chromate or manganese dioxide or aluminium isopropoxide or phenoxide in the presence of carbonyl compounds. The hydrogenation may be carried out using zinc and acetic acid. The ketals may be prepared by known methods. In examples: 2 : 6 : 6-trimethyl - cyclohexen - (2) - ol - (1) - one - (4) was oxidized with chromic acid to give 2 : 6 : 6-trimethyl - cyclohexen - (2) - dione - (1 : 4) which was reduced with zinc and acetic acid to give 2 : 6 : 6 - trimethyl - cyclohexanedione - (1 : 4). The phenylsemicarbazones of both ketones were prepared. The 4 : 4-ethylenedioxy derivatives of both diketones were prepared by heating them with ethylene glycol in the presence of p-toluene sulphonic acid and distilling off the water formed.
GB2098756A 1956-07-06 1956-07-06 Novel cyclic diketones and ketals thereof and a process for the manufacture of the same Expired GB791953A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2098756A GB791953A (en) 1956-07-06 1956-07-06 Novel cyclic diketones and ketals thereof and a process for the manufacture of the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2098756A GB791953A (en) 1956-07-06 1956-07-06 Novel cyclic diketones and ketals thereof and a process for the manufacture of the same

Publications (1)

Publication Number Publication Date
GB791953A true GB791953A (en) 1958-03-19

Family

ID=41111382

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2098756A Expired GB791953A (en) 1956-07-06 1956-07-06 Novel cyclic diketones and ketals thereof and a process for the manufacture of the same

Country Status (1)

Country Link
GB (1) GB791953A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2657386A1 (en) * 1975-12-19 1977-06-30 Rhone Poulenc Ind PROCESS FOR THE PREPARATION OF 3,5,5-TRIMETHYLCYCLOHEXEN-2-DIONE-1,4
WO2001087811A1 (en) * 2000-05-17 2001-11-22 Degussa Ag Process for the production of 2,2,6-trimethylcyclohexane-1,4-dione
US6469215B1 (en) 2000-05-17 2002-10-22 Degussa Ag Process for the production of an intermediate mixture of β-isophorone epoxide and its isomer 4-hydroxyisophorone (HIP)
CN109503545A (en) * 2018-11-30 2019-03-22 彩客化学(沧州)有限公司 A kind of preparation method of 1,4- cyclohexanedione monoethylene acetal

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2657386A1 (en) * 1975-12-19 1977-06-30 Rhone Poulenc Ind PROCESS FOR THE PREPARATION OF 3,5,5-TRIMETHYLCYCLOHEXEN-2-DIONE-1,4
WO2001087811A1 (en) * 2000-05-17 2001-11-22 Degussa Ag Process for the production of 2,2,6-trimethylcyclohexane-1,4-dione
US6420609B2 (en) 2000-05-17 2002-07-16 Degussa Ag Process for the production of 2,2,6-trimethylcyclohexane-1,4-dione
US6469215B1 (en) 2000-05-17 2002-10-22 Degussa Ag Process for the production of an intermediate mixture of β-isophorone epoxide and its isomer 4-hydroxyisophorone (HIP)
CN109503545A (en) * 2018-11-30 2019-03-22 彩客化学(沧州)有限公司 A kind of preparation method of 1,4- cyclohexanedione monoethylene acetal

Similar Documents

Publication Publication Date Title
GB799270A (en) Production of intermediates for the synthesis of reserpine and allied compounds
NL7501765A (en) PROCESS FOR THE WINNING OF TECHNICALLY PURE ACETIC ACID BY AN EXTRACTIVE DISTILLATION.
GB791953A (en) Novel cyclic diketones and ketals thereof and a process for the manufacture of the same
Shine A New Technique in Preparing 2, 4-Dinitrophenylhydrazones. Use of Diglyme as Solvent
GB1429120A (en) Preparation of a diketone
GB1416975A (en) Production of high molecular weight unsaturated ketones
GB1100480A (en) Process for producing methoxyphenol or ethoxyphenol
GB1101955A (en) Process for the selective preparation of a cyclic ketone
GB1089788A (en) Process for the production of steroidal lactone compounds and intermediates thereof
GB1380555A (en) Process for the preparation of 2,3,5-trimethylhydroquinone
SETA et al. Biochemical Studies on “Bakanae” Fungus. Part 52 Chemical Structure of Gibberellins. Part XVIII
GB467376A (en) Process for the manufacture of unsaturated neutral oxidation products of stigmasterol compounds
GB918900A (en) Production of cyclohexanone and cyclohexanol
Harrison et al. Taxine. Part III. A revised structure for the neutral fragment from O-cinnamoyltaxicin-I
Kuwata Stereochemistry of Pinocampheols
STODOLA et al. Studies on steroid α-ketols. I. The partial synthesis of 16-ketotestosterone acetate
GB1412928A (en) Process for the manufacture of methyl vinyl ketone
GB828591A (en) Novel bicyclic compounds and a process for the manufacture thereof
ES447636A1 (en) Process for manufacture of 3,5-ditert.butyl-4-hydroxybenzaldehyde from 3,5-ditert.butyl-4-hydroxybenzyl alcohol
GB1073884A (en) Process for oxidizing a 1,1-bis-(alkylphenyl) alkane
GB958092A (en) 12-hydroxyiminosteroids and production thereof
GB508305A (en) Process for the manufacture of pregnendione
LaForge et al. ROTENONE. II. THE DERIVATIVES OF DERRITOL1
IE34082B1 (en) A process for the preparation of 3-oxo-19-nor-delta4-steroids via novel nitrogenous 4,5-secosteroids
GB1216013A (en) Production of 2,6-dimethylphenol