GB1119612A - Hydroxylation of alkenyl substituted aromatic compounds - Google Patents

Hydroxylation of alkenyl substituted aromatic compounds

Info

Publication number
GB1119612A
GB1119612A GB1728766A GB1728766A GB1119612A GB 1119612 A GB1119612 A GB 1119612A GB 1728766 A GB1728766 A GB 1728766A GB 1728766 A GB1728766 A GB 1728766A GB 1119612 A GB1119612 A GB 1119612A
Authority
GB
United Kingdom
Prior art keywords
methyl ether
substituted aromatic
oxidizing agent
alkenyl
denotes
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
GB1728766A
Inventor
John Dobney Andrew Johnson
Egbert Mead Gibbs
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.)
WJ Bush and Co Ltd
Original Assignee
WJ Bush and Co Ltd
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 WJ Bush and Co Ltd filed Critical WJ Bush and Co Ltd
Priority to GB1728766A priority Critical patent/GB1119612A/en
Publication of GB1119612A publication Critical patent/GB1119612A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/52—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule

Abstract

Vicinal glycols are obtained by treating alkenyl-substituted aromatic compounds of the formula <FORM:1119612/C2/1> in which R1 denotes a group containing an olefinic bond, R2 denotes an inert substituant, preferably an alkoxy or methylenedioxy group, and n is 0-2, with a peroxidic oxidizing agent under acid conditions in the presence of at least 50% by volume of water based on the total volume of alkenyl-substituted aromatic compound and oxidizing agent. The oxidizing agent may be an organic or inorganic peroxide, hydroperoxide or peracid, specified oxidizing agents being performic and peracetic acids and hydrogen peroxide. The reaction may be effected at 15-50 DEG C. and the reaction mixture may include an emulsifying agent, e.g. cetylpyridinium chloride. Examples are given in which isoeugenol methyl ether is treated with peracetic acid or with hydrogen peroxide and formic acid, respectively, to yield a glycol of the formula <FORM:1119612/C2/2> Other specified starting materials are anethole and isosafrole. Aromatic ketones are obtained by distilling the glycols obtained as described above in the presence of a dehydrating agent. An example is given in which the glycol formulated above is vacuum-distilled in the presence of anhydrous zinc chloride to yield 3,4-dimethoxyphenylacetone. Isoeugenol methyl ether, used in examples 1 and 2, is obtainable by heating eugenol methyl ether with alcoholic potassium hydroxide.
GB1728766A 1966-04-20 1966-04-20 Hydroxylation of alkenyl substituted aromatic compounds Expired GB1119612A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1728766A GB1119612A (en) 1966-04-20 1966-04-20 Hydroxylation of alkenyl substituted aromatic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1728766A GB1119612A (en) 1966-04-20 1966-04-20 Hydroxylation of alkenyl substituted aromatic compounds

Publications (1)

Publication Number Publication Date
GB1119612A true GB1119612A (en) 1968-07-10

Family

ID=10092559

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1728766A Expired GB1119612A (en) 1966-04-20 1966-04-20 Hydroxylation of alkenyl substituted aromatic compounds

Country Status (1)

Country Link
GB (1) GB1119612A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025892A1 (en) * 1979-09-19 1981-04-01 Degussa Aktiengesellschaft Process for the hydroxylation of styrene and of styrene derivatives
DE2937810A1 (en) * 1979-09-19 1981-04-02 Degussa Ag, 6000 Frankfurt METHOD FOR HYDROXYLATING CYCLIC OLEFINS WITH ONE OR TWO DOUBLE BINDINGS
DE2937840A1 (en) * 1979-09-19 1981-04-02 Degussa Ag, 6000 Frankfurt METHOD FOR THE HYDROXYLATION OF SHORT-CHAIN ALIPHATIC MONO- OR DIOLEFINS
EP0247526A2 (en) * 1986-05-22 1987-12-02 LARK S.p.A. Process for 3,4-dimethoxyphenyl-acetone preparation
US4967009A (en) * 1988-07-08 1990-10-30 Nippon Petrochemicals Co., Ltd. Method for oxidizing unsaturated aromatic compounds

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025892A1 (en) * 1979-09-19 1981-04-01 Degussa Aktiengesellschaft Process for the hydroxylation of styrene and of styrene derivatives
DE2937810A1 (en) * 1979-09-19 1981-04-02 Degussa Ag, 6000 Frankfurt METHOD FOR HYDROXYLATING CYCLIC OLEFINS WITH ONE OR TWO DOUBLE BINDINGS
DE2937840A1 (en) * 1979-09-19 1981-04-02 Degussa Ag, 6000 Frankfurt METHOD FOR THE HYDROXYLATION OF SHORT-CHAIN ALIPHATIC MONO- OR DIOLEFINS
DE2937768A1 (en) * 1979-09-19 1981-04-16 Degussa Ag, 6000 Frankfurt METHOD FOR HYDROXYLATING STYRENE AND STYRENE DERIVATIVES
EP0247526A2 (en) * 1986-05-22 1987-12-02 LARK S.p.A. Process for 3,4-dimethoxyphenyl-acetone preparation
EP0247526A3 (en) * 1986-05-22 1989-04-12 LARK S.p.A. Process for 3,4-dimethoxyphenyl-acetone preparation
US4967009A (en) * 1988-07-08 1990-10-30 Nippon Petrochemicals Co., Ltd. Method for oxidizing unsaturated aromatic compounds

Similar Documents

Publication Publication Date Title
Žmitek et al. α-Substituted organic peroxides: synthetic strategies for a biologically important class of gem-dihydroperoxide and perketal derivatives
AR247203A1 (en) 5-arylalkyl-4-alkoxy-2(5h)-furanones, intermediates and process for their preparation as well as their application as therapeutically active ingredients
DK15691D0 (en) (1R, CIS) -2,2-DIMETHYL-3- (2-HALOGEN-2- (SUBSTITUTED HYDROXY) CARBONYLETHENYL) CYCLOPROPAN-1-CARBOXYL ACID
GB1119612A (en) Hydroxylation of alkenyl substituted aromatic compounds
CH626885A5 (en)
US4590286A (en) Process for epoxidizing an olefin
ARNETT Reaction of Benzyne With An Allylic Olefin
Cope et al. Amine Oxides. II. Conversion to N, N-Dialkylhydroxylamines1
Ogata et al. Oxidation of trans-stilbene with peroxymonophosphoric acid
CA1080727A (en) Preparation of epoxides
JPS5452043A (en) Preparation of peroxide
ATE14427T1 (en) PROCESS FOR THE MANUFACTURE OF EPSILON CAPROLACTAM.
GB941507A (en) Epoxy isocyanurate compounds
CH626614A5 (en) Process for the epoxidation of olefins in the presence of arsenic-based catalysts
GB956115A (en) Improvements in or relating to a process for the preparation of organic peroxides
GB802022A (en) Dioxolanes
Linn et al. Tetracyanoethylene Oxide
US2598040A (en) 4-(1,2-dihydroxyethyl)-1,3-dioxane
GB944408A (en) New epoxides, process for their preparation, and compositions containing them
US5973209A (en) Method for preparing 3, 3-dimethybutyraldehyde
Rozen et al. The First, General, Highly Efficient Method for Preparing Tetrasubstituted Epoxides Using HOF· CH3CN
US2606209A (en) 4, 4-di (chloromethyl)-2-pentanone
US3867457A (en) Preparation of ninhydrin
JPS57108062A (en) 3-perfluoroalkylsulfonyl-1,2-propanediol
JPS54145604A (en) Preparation of diols