SU680641A3 - Method of obtaining 3-brombenzaldehyde - Google Patents
Method of obtaining 3-brombenzaldehydeInfo
- Publication number
- SU680641A3 SU680641A3 SU762363456A SU2363456A SU680641A3 SU 680641 A3 SU680641 A3 SU 680641A3 SU 762363456 A SU762363456 A SU 762363456A SU 2363456 A SU2363456 A SU 2363456A SU 680641 A3 SU680641 A3 SU 680641A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- bromine
- mixture
- benzaldehyde
- bromobenzaldehyde
- mol
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
-
- 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
- C07C45/63—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 halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
II
Изобретение относитс к способам получени замещенных бензальдегидов , конкретно к способу получени 3-бромбензальдегида, вл ющегос промежуточным продуктом дл получени производных 3-феноксибензилового спирта, которые образуют инсектицидно-активные эфиры с некоторыми карбоновыми кислотами.The invention relates to methods for producing substituted benzaldehydes, specifically to a method for producing 3-bromobenzaldehyde, which is an intermediate product for obtaining 3-phenoxybenzyl alcohol derivatives, which form insecticidal esters with certain carboxylic acids.
Известен способ получени 3-бромбензальдегида бронированием бензальдегида молекул рным бромом в присутствии хлористого алюмини при мол рном соотношении реагентов - брома и бензальдегида - 1,1:1 в среде 1,2-дихлорэтана при температуре 3545°С . Выход целевого продукта составл ет 70% 1 . A known method for producing 3-bromobenzaldehyde by reserving benzaldehyde with molecular bromine in the presence of aluminum chloride at a molar ratio of reagents - bromine and benzaldehyde is 1.1: 1 in 1,2-dichloroethane at a temperature of 3545 ° C. The yield of the target product is 70% 1.
Недостатками известного способа получени 3-бромбензальдегида вл ютс большой расход брома и недостаточно высокий выход целевого продукта.The disadvantages of the known method for producing 3-bromobenzaldehyde are the high consumption of bromine and the insufficiently high yield of the target product.
Целью изобретени вл етс увеличение выхода целевого продукта и снижение его себестоимости.The aim of the invention is to increase the yield of the target product and reduce its cost.
Указанна цель достигаетс способом получени 3-бромбензальдегида бромированием бензальдегида в среде хлорированного алкана и вThis goal is achieved by the method of producing 3-bromobenzaldehyde by brominating benzaldehyde in a chlorinated alkane medium and in
присутствии хлористого алюмини смесью хлора и брома при мол рном соотношении 0,90-1,0:1,0 соответственно , при температуре 3-25°С. Хлор и бром можно либо смешать -до контакта с бензальдегидом, например , ПО.ПУЧИВ их раствор в хлорированном углеводороде (предпочтительный вариант), либо можно ввести по отдельности хлор и бром в смесь бензальдегида, хлористого а.шомини и растворител .the presence of aluminum chloride with a mixture of chlorine and bromine at a molar ratio of 0.90-1.0: 1.0, respectively, at a temperature of 3-25 ° С. Chlorine and bromine can either be mixed - up to contact with benzaldehyde, for example, by removing their solution in chlorinated hydrocarbon (the preferred option), or you can introduce chlorine and bromine separately into a mixture of benzaldehyde, A.shominy chloride and a solvent.
Отличительными признаками способа вл ютс : осуществление бромировани смесью хлора и брома прк мол рном соотношении 0,9-1,0:1,0 соответственно и проведение процесса при температуре 3- 2 . П р и м е р -1. 0,5 моль хлораDistinctive features of the method are: the implementation of bromination with a mixture of chlorine and bromine at a molar ratio of 0.9-1.0: 1.0, respectively, and carrying out the process at a temperature of 3-2. PRI me R -1. 0.5 mole chlorine
.добавл ют к раствору 0,5 моль брома в 20 мл 1,2-дихлорэтана, охлажденному твердым СО2 в изопропаноле, и полученный раствор разбавл ют 100 мл 1,2-дихлорэтана. Полученный раствор добавл ют в течение 2 ч 20 мин к смеси 1,3 моль хлорида а.шомнни и 1,0 моль бензальдегида в 200 мл 1,2-дихлорэтана при 23-25 С. Затем смесь перемешивают еще 1 ч при этой температуре.Add a solution of 0.5 mol of bromine in 20 ml of 1,2-dichloroethane, cooled by solid CO2 in isopropanol, and the resulting solution is diluted with 100 ml of 1,2-dichloroethane. The resulting solution is added over a period of 2 hours and 20 minutes to a mixture of 1.3 mol of chloride of ash and 1.0 mol of benzaldehyde in 200 ml of 1,2-dichloroethane at 23–25 ° C. The mixture is then stirred for another 1 hour at this temperature.
На этой стадии конверси бензальдегида составл ет 89% и селективность по 3-бромбензальдегиду 9596% (по данным ГЖХ).At this stage, the conversion of benzaldehyde is 89% and the selectivity for 3-bromobenzaldehyde is 9596% (according to GLC).
Реакционную смесь разбавл ют достаточным количеством воды дл растворени осадка гидроокиси алюмини . Отдел ют органический слой, про ывают его 100 мл воды и сушат (сульфат магни ). Растворитель отгон ют, остаток подвергают фракционной перегонке и получают 3-бромбензальдегид, т.кип при 1,5 мм рт.ст., выход 79%,.The reaction mixture is diluted with enough water to dissolve the aluminum hydroxide precipitate. The organic layer is separated, washed with 100 ml of water and dried (magnesium sulfate). The solvent is distilled off, the residue is subjected to fractional distillation and 3-bromobenzaldehyde is obtained, b.p. at 1.5 mm Hg, 79% yield ,.
При мер 2. 1,3 моль бензальдегида добавл ют в течение 0,75, ч JC смеси 1,43 моль хлорида алюмини и 500 мл 1,2-дихлорэтана при . Добавл ют 0,65 моль жидкого брома к смеси при 15с, в полученную сме пропускают газообразный хлор приExample 2. 1.3 mol of benzaldehyde was added over 0.75 h, JC of a mixture of 1.43 mol of aluminum chloride and 500 ml of 1,2-dichloroethane at. 0.65 mol of liquid bromine is added to the mixture at 15 s, chlorine gas is passed into the mixture at
Услови проведени реакции брог«1ровани бензальдег«да и выход 3-бромбензальдегидаConditions for the reaction of the brog "1benzaldeg" and the yield of 3-bromobenzaldehyde
,15С в течение 2 ч до достижени мол рного соотношени хлора к брому 0,95:1. Смесь перемешивают еще 1 ч при . Добавл ют раствор 0,0355 моль муравьиной кислоты в 500 мл воды к реакционной смеси дл разрушени избытка брома. Органический слой отдел ют, промывают 500 мл воды, содержащей тиххзульфат натри (дл промотировани разделени ) и затем 500 мл воды. Промывные воды собирают и экстрагируют 250 МП 1,2-дихлорэтаиа. Собирают две органические фазы и подвергают анализу ГЖХ. Результаты приведены в таблице., 15 ° C for 2 hours until a molar ratio of chlorine to bromine reaches 0.95: 1. The mixture is stirred for another 1 h at. A solution of 0.0355 mol of formic acid in 500 ml of water is added to the reaction mixture to destroy the excess bromine. The organic layer is separated, washed with 500 ml of water containing sodium silent sulfate (to promote separation) and then 500 ml of water. Wash water is collected and extracted with 250 MP of 1,2-dichloroethane. Collect the two organic phases and analyze by GLC. The results are shown in the table.
Примеры 3-19. Реакцию провод т в услови х примера 2. Услови проведени реакций и результаты приведены в таблице.Examples 3-19. The reaction is carried out under the conditions of Example 2. The reaction conditions and results are shown in the table.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB23771/75A GB1535333A (en) | 1975-06-02 | 1975-06-02 | Process for the preparation of 3-bromo-benzaldehyde |
GB33076 | 1976-01-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
SU680641A3 true SU680641A3 (en) | 1979-08-15 |
Family
ID=26235853
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU762363456A SU680641A3 (en) | 1975-06-02 | 1976-05-31 | Method of obtaining 3-brombenzaldehyde |
Country Status (15)
Country | Link |
---|---|
JP (1) | JPS51143639A (en) |
BR (1) | BR7603452A (en) |
CA (1) | CA1069135A (en) |
CH (1) | CH620188A5 (en) |
DD (1) | DD124377A5 (en) |
DE (1) | DE2624410A1 (en) |
DK (1) | DK238776A (en) |
FR (1) | FR2313339A1 (en) |
HU (1) | HU174975B (en) |
IE (1) | IE42828B1 (en) |
IL (1) | IL49688A (en) |
IT (1) | IT1060880B (en) |
LU (1) | LU75056A1 (en) |
NL (1) | NL7605829A (en) |
SU (1) | SU680641A3 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3136561A1 (en) * | 1981-09-15 | 1983-03-31 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING PARA-SUBSTITUTED 3-BOMBENZALDEHYDES |
US4585898A (en) * | 1984-12-18 | 1986-04-29 | Hardwicke Chemical Company | Preparation of substituted benzaldehydes |
-
1976
- 1976-05-03 CA CA251,701A patent/CA1069135A/en not_active Expired
- 1976-05-31 IE IE1152/76A patent/IE42828B1/en unknown
- 1976-05-31 LU LU75056A patent/LU75056A1/xx unknown
- 1976-05-31 SU SU762363456A patent/SU680641A3/en active
- 1976-05-31 JP JP51062450A patent/JPS51143639A/en active Pending
- 1976-05-31 IL IL49688A patent/IL49688A/en unknown
- 1976-05-31 NL NL7605829A patent/NL7605829A/en not_active Application Discontinuation
- 1976-05-31 BR BR3452/76A patent/BR7603452A/en unknown
- 1976-05-31 CH CH680876A patent/CH620188A5/en not_active IP Right Cessation
- 1976-05-31 DD DD193100A patent/DD124377A5/xx unknown
- 1976-05-31 IT IT23799/76A patent/IT1060880B/en active
- 1976-05-31 DE DE19762624410 patent/DE2624410A1/en not_active Withdrawn
- 1976-05-31 DK DK238776A patent/DK238776A/en not_active Application Discontinuation
- 1976-05-31 HU HU76SE1836A patent/HU174975B/en unknown
- 1976-05-31 FR FR7616353A patent/FR2313339A1/en active Granted
Also Published As
Publication number | Publication date |
---|---|
IL49688A0 (en) | 1976-07-30 |
AU1444576A (en) | 1977-12-08 |
IL49688A (en) | 1978-12-17 |
FR2313339B1 (en) | 1978-11-17 |
DD124377A5 (en) | 1977-02-16 |
DK238776A (en) | 1976-12-03 |
DE2624410A1 (en) | 1976-12-16 |
IT1060880B (en) | 1982-09-30 |
BR7603452A (en) | 1977-01-04 |
FR2313339A1 (en) | 1976-12-31 |
IE42828L (en) | 1976-12-02 |
JPS51143639A (en) | 1976-12-10 |
HU174975B (en) | 1980-04-28 |
CA1069135A (en) | 1980-01-01 |
IE42828B1 (en) | 1980-10-22 |
CH620188A5 (en) | 1980-11-14 |
LU75056A1 (en) | 1977-02-15 |
NL7605829A (en) | 1976-12-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SU680641A3 (en) | Method of obtaining 3-brombenzaldehyde | |
Payne | Alkaline Epoxidation of α, β-Unsaturated Aldehydes | |
Cason et al. | Branched-chain fatty acids. XXIV. Synthesis of 2-methyl-2-dodecenoic acid and of 2-methylenedodecanoic acid | |
SU843732A3 (en) | Method of preparing substituted indanylcateic acid | |
SU554809A3 (en) | The method of obtaining cyclopropane carboxylic acids | |
SU910113A3 (en) | Process for producing 3-phenoxybenzaldehyde derivatives | |
CRAGOE Jr et al. | Synthetic Antiviral Agents. I. 4-Arylmethyl-4-aryl-5-oxohexanoic Acids and Certain of Their Derivatives*, 1 | |
SU457210A3 (en) | Method for producing benzoyl- (3-phenyl) -2-propionic or benzoyl- (3-phenyl) acetic acid | |
KOBAYASHI et al. | Studies on organic fluorine compounds. XXII. Synthesis and reactions of (trifluoromethyl) benzofurans | |
Horning et al. | Polymethoxybromobenzenes1 | |
Warnhoff et al. | α-Halo ketones. V. Synthesis of some bicyclic bridgehead bromo ketones | |
Shive et al. | The Synthesis and Characterization of Some Tertiary Naphthenic Acids | |
Braun et al. | Esters of β-Diazopropionic Acid. A New Synthesis of β-Aryloxypropionic Acids1, 2 | |
MEYER et al. | Alkylations at the α-Carbon of Phenylacetamide and Phenylacetic Acid Through Their Disodio Salts1 | |
US4191841A (en) | Process for manufacturing 4-hydroxy-3,5-dimethoxy benzoic acid from 3,4,5-trimethoxybenzoic acid | |
JPS6230181B2 (en) | ||
SHECHTER et al. | I. Addition Reactions of Arylalkanes and Maleic Anhydride Occurring by Chain Processes | |
US4143229A (en) | Process for the preparation of para-substituted derivatives of alpha-phenylpropionic acid | |
SU1313851A1 (en) | Method for producing 1-aminocyclopropane-1-carboxylic acid | |
Adkins et al. | β-tetralone | |
Hachihama et al. | Chlorination of Furfural in Concentrated Hydrochloric Acid | |
JP4304758B2 (en) | Method for producing para-acetoxystyrene | |
Palameta et al. | Stereospecific Syntheses of Long-Chain 1, 2, 3, 4-Alkanetetrols | |
Allen et al. | The Action of Sulphuric Acid on Certain Derivatives of Cyclopropane | |
SU973524A1 (en) | Process for producing dimethyl ester of tricyclo-(4,2,0 2.5)deca-3,7-diene-9,10-cis-endo-dicarboxylic acid |