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GB1316739A - Preparation of acetates of monohydric and dihydric phenols - Google Patents

Preparation of acetates of monohydric and dihydric phenols

Info

Publication number
GB1316739A
GB1316739A GB1316739DA GB1316739A GB 1316739 A GB1316739 A GB 1316739A GB 1316739D A GB1316739D A GB 1316739DA GB 1316739 A GB1316739 A GB 1316739A
Authority
GB
United Kingdom
Prior art keywords
contacted
acetic anhydride
mole ratios
cone
mixture
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
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.)
Texaco Development Corp
Original Assignee
Texaco Development Corp
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 Texaco Development Corp filed Critical Texaco Development Corp
Publication of GB1316739A publication Critical patent/GB1316739A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1316739 Benzene acetates and diacetates TEXACO DEVELOPMENT CORP 20 Oct 1971 48680/71 Heading C2C Benzene acetates and diacetates and alkyl derivatives thereof are obtained by reacting cyclohexanone derivatives of the formulµ wherein R is H or (C 1 -C 20 ) alkyl, R<SP>1</SP> is (C 1 - C 20 ) alkyl, X is H or halogen, at least one being halogen, Y is a keto oxygen atom, with acetic anhydride and cone. H 2 SO 4 . In particular embodiments (i) a halocyclohexanone of Formula I is contacted firstly with a mixture of acetic anhydride and a catalytic amount of cone. H 2 SO 4 , cone. HCl, pyridine or BF 3 etherate at 30‹ to 150‹ C. in specified mole ratios, subsequently the first reaction mixture is contacted with cone. H 2 SO 4 at 30‹ to 150‹ C. in specified mole ratios and recovering catechol diacetate from the second reaction mixture; (ii) a 2- acetoxycyclohexanone of Formula II is contacted firstly with a mixture of BF 3 etherate, acetic anhydride at 30‹ to 500‹ C. in specified mole ratios, subsequently the first reaction mixture is contacted with cone. H 2 SO 4 at 30‹ to 500‹ C. in specified mole ratios; (iii) a cyclohexanone of Formula III is contacted with a mixture of conc. H 2 SO 4 and acetic anhydride, in specified mole ratios, at 30‹ to 150‹ C.; (iv) a cyclohexanedione of Formula IV is contacted with a mixture of cone. H 2 SO 4 and acetic anhydride, in specified mole ratios, at a temperature of at least 30‹ C.; and (v) a gempolyalkylat-d cyclohexanedione of Formula V where both R groups and both R<SP>1</SP> groups are in the gem positions, the gem carbons being adjacent to at least one unsubstituted carbon in the ring, is contacted with a mixture of conc. H 2 SO 4 and acetic anhydride in specified mole ratios, at a temperature of at least 30‹ C. Examples are given which illustrate these embodiments. Mono- and di-hydroxy benzenes optionally containing alkyl groups may be obtained by acid hydrolysis of the corresponding acetates. Halocyclohexanones and alkyl halocyclohexanones may be obtained by halogenating the corresponding cyclohexanone or cyclohexanol with free halogen. 2-Acetoxycyclohexanone is obtained by reacting 1-cyclohexenyl acetate with tert-butyl hydroperoxide. 1-Cyclohexenyl acetate is obtained by reacting cyclohexanone with acetic anhydride.
GB1316739D 1971-10-20 1971-10-20 Preparation of acetates of monohydric and dihydric phenols Expired GB1316739A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4868071 1971-10-20

Publications (1)

Publication Number Publication Date
GB1316739A true GB1316739A (en) 1973-05-16

Family

ID=10449527

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1316739D Expired GB1316739A (en) 1971-10-20 1971-10-20 Preparation of acetates of monohydric and dihydric phenols

Country Status (1)

Country Link
GB (1) GB1316739A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0185522A3 (en) * 1984-12-14 1987-07-01 The Clorox Company Phenylene mono- and diester peracid percursors
US4814110A (en) * 1984-12-14 1989-03-21 The Clorox Company Method for esterifying dihydroxybenzenes
US5290793A (en) * 1989-09-12 1994-03-01 Mitsui Toatsu Chemicals, Incorporated Dihydrocaffeic acid derivatives and pharmaceutical preparation containing same
EP0850912A1 (en) * 1996-12-27 1998-07-01 Daicel Chemical Industries, Ltd. Trimethylcatechol diester and a method for producing the same

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0185522A3 (en) * 1984-12-14 1987-07-01 The Clorox Company Phenylene mono- and diester peracid percursors
US4814110A (en) * 1984-12-14 1989-03-21 The Clorox Company Method for esterifying dihydroxybenzenes
US5290793A (en) * 1989-09-12 1994-03-01 Mitsui Toatsu Chemicals, Incorporated Dihydrocaffeic acid derivatives and pharmaceutical preparation containing same
EP0850912A1 (en) * 1996-12-27 1998-07-01 Daicel Chemical Industries, Ltd. Trimethylcatechol diester and a method for producing the same
US5955628A (en) * 1996-12-27 1999-09-21 Daicel Chemical Industries, Ltd. Trimethylcatechol diester and a method for producing the same
CN1125028C (en) * 1996-12-27 2003-10-22 大赛璐化学工业株式会社 The method for preparing trimethylcatechol diester

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees