GB288441A - Manufacture of cyclic ketones of the aromatic series - Google Patents

Manufacture of cyclic ketones of the aromatic series

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Publication number
GB288441A
GB288441A GB1118727A GB1118727A GB288441A GB 288441 A GB288441 A GB 288441A GB 1118727 A GB1118727 A GB 1118727A GB 1118727 A GB1118727 A GB 1118727A GB 288441 A GB288441 A GB 288441A
Authority
GB
United Kingdom
Prior art keywords
acid
similarly obtained
indanone
methyl
similarly
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
GB1118727A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB1118727A priority Critical patent/GB288441A/en
Publication of GB288441A publication Critical patent/GB288441A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions

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  • 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)

Abstract

288,441. Imray, O. Y., (I. G. Farbenindustrie Akt.-Ges.). April 26, 1927. Cyclic ketones are obtained by heating aromatic hydrocarbons or their homologues or substitution products with olefine carboxylic acids or their hydrogen halide addition products and an acid condensing agent in absence or pnesence of a solvent. In examples, (1) benzene is condensed with #-chloropropionic acid in presence of aluminium chloride, and the 1-indanone produced is separated by distillation; (2) a mixture of 4- and 6-methyl-1-indanones is similarly obtained from toluene; (3) 4- and 6-chloro-1-indanones are similarly obtained from chlorobenzene and are separated by crystallization, and corresponding products are similarly obtained from bromobenzene, o- and m-dichlorobenzene, m-dibromobenzene, and o-chlorotoluene; (4) benzene is similarly condensed with #-chlorobutyric acid to obtain 3-methyl-1-indanone; (5) a mixture of 4- and 6-chloro-3-methyl-1-indanones is similarly obtained from chlorobenzene; (6) 3 : 4: 8-trimethyl- 1-indanone is similarly obtained from m-xylene; (7) chlorobenzene is condensed with crotonic acid in presence of aluminium chloride to obtain the mixture of example (5); (8) 4: 6-dichloro-3- methyl-1-indanone is similarly obtained from mdichlorobenzene, and corresponding products are similarly obtained from o-dichlorobenzene, bromobenzene, and m-xylene; (9) naphthalene dissolved in nitrobenzene is treated with cinnamic acid in presence of 85 per cent sulphuric acid at 45‹ C., and the resinous mass of naphthylphenylpropionic acid produced is treated in nitrobenzene solution with phosphorus pentachloride and aluminium chloride, and the cyclic ketone obtained is purified by boiling with sodium carbonate solution, distillation in vacuo, and re-crystallization.
GB1118727A 1927-04-26 1927-04-26 Manufacture of cyclic ketones of the aromatic series Expired GB288441A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1118727A GB288441A (en) 1927-04-26 1927-04-26 Manufacture of cyclic ketones of the aromatic series

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1118727A GB288441A (en) 1927-04-26 1927-04-26 Manufacture of cyclic ketones of the aromatic series

Publications (1)

Publication Number Publication Date
GB288441A true GB288441A (en) 1928-04-12

Family

ID=9981606

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1118727A Expired GB288441A (en) 1927-04-26 1927-04-26 Manufacture of cyclic ketones of the aromatic series

Country Status (1)

Country Link
GB (1) GB288441A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497673A (en) * 1946-04-16 1950-02-14 Du Pont Reaction of alpha-beta unsaturated compounds with aromatic hydrocarbons and products obtained
US3950408A (en) * 1974-02-15 1976-04-13 Merck & Co., Inc. Process for preparing [1-oxo-2-cyclopentyl (or 2-isopropyl)-2-methyl-6,7-dichloro-5-indanyloxy] acetic acid

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497673A (en) * 1946-04-16 1950-02-14 Du Pont Reaction of alpha-beta unsaturated compounds with aromatic hydrocarbons and products obtained
US3950408A (en) * 1974-02-15 1976-04-13 Merck & Co., Inc. Process for preparing [1-oxo-2-cyclopentyl (or 2-isopropyl)-2-methyl-6,7-dichloro-5-indanyloxy] acetic acid

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