US4342877A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the preparation of α-halogenated cresol esters
Assignee: Eastman Chemical Co
•
Filing: 1979-11-13
•
Granted: 1982-08-03
•
Expires: 1999-11-13
Abstract
Abstract Process for the preparation of Compound I by treating Compound II with X 2 or SO 2 X 2 in the presence of a free radical initiator and an anhydride having the formula (RCO) 2 O while eliminating the acid halide formed having the formula RCOX from the reaction mixture, wherein Compounds I and II have the formulas ##STR1## and R is C 1 -C 3 alkyl, X is Cl or Br and n is 1, 2 or 3.
Inventors
- 👤 Dah-Chieh O. Cheng
- 👤 Joseph S. Bowers, Jr.
- 👤 Ronald J. Maner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 22:53
CPC Classifications
C; C07; C07C; C07C67/00; C07C67/28; C07C67/287
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
89 words
Process for the preparation of Compound I by treating Compound II with X 2 or SO 2 X 2 at a temperature of about 60° to 85° C. in the presence of a halogenation-promoting free radical initiator and an anhydride having the formula (RCO) 2 O while eliminating the acid halide formed having the formula RCOX from the reaction mixture, wherein Compounds I and II have the formulas ##STR3## and R is C 1 -C 3 alkyl, X is Cl or Br and n is 1, 2 or 3.
Claim 2
Dependent Claim
89 words
Process for the preparation of Compound I by treating Compound II with X 2 or SO 2 X 2 at a temperature of about 60° to 85° C. in the presence of a halogenation-promoting free radical initiator and an anhydride having the formula (RCO) 2 O while eliminating the acid halide formed having the formula RCOX from the reaction mixture, wherein Compounds I and II have the formulas ##STR3## and R is C 1 -C 3 alkyl, X is Cl or Br and n is 1, 2 or 3.
Claim 3
Dependent Claim
37 words
Process according to claim 1 wherein the acid halide is eliminated by carrying out the process in the presence of an alkali metal salt of a C 2 -C 4 carboxylic acid or an alkali metal carbonate.
Claim 4
Dependent Claim
28 words
Process according to claim 1 wherein the acid halide is eliminated by carrying out the process under reduced pressure while distilling the acid halide from the reaction mixture.
Claim 5
Dependent Claim
77 words
Process for the preparation of Compound I which comprises treating Compound II with about 0.6 to 1.0 mole of X 2 or SO 2 X 2 per mole of Compound II at a temperature of about 60° to 85° C. in the presence of a halogenation-promoting free radical initiator and acetic anhydride while eliminating the acetyl halide formed from the reaction mixture, wherein Compounds I and II have the formulas ##STR4## and X is Cl or Br.
Claim 6
Dependent Claim
77 words
Process for the preparation of Compound I which comprises treating Compound II with about 0.6 to 1.0 mole of X 2 or SO 2 X 2 per mole of Compound II at a temperature of about 60° to 85° C. in the presence of a halogenation-promoting free radical initiator and acetic anhydride while eliminating the acetyl halide formed from the reaction mixture, wherein Compounds I and II have the formulas ##STR4## and X is Cl or Br.
Claim 7
Dependent Claim
54 words
Process according to claim 4 wherein the acid halide is eliminated by carrying out the process in the presence of at least one equivalent of an alkali metal salt of a C 2 -C 4 carboxylic acid or an alkali metal carbonate and the free radical initiator is azobisisobutyronitrile, dibenzoyl peroxide or di-t-butyl peroxide.
Claim 8
Dependent Claim
20 words
Process according to claim 5 wherein X is Cl, Compound I is p-acetoxybenzyl chloride and Compound II is p-tolyl acetate.
Claim 9
Dependent Claim
41 words
Process according to claim 4 wherein the acid halide is eliminated by carrying out the process under reduced pressure while distilling the acid halide from the reaction mixture and wherein the free radical initiator is azobisisobutyronitrile, dibenzoyl peroxide or di-t-butyl peroxide.
Claim 10
Dependent Claim
20 words
Process according to claim 7 wherein X is Cl, Compound I is p-acetoxybenzyl chloride and Compound II is p-tolyl acetate.
Claim 11
Dependent Claim
73 words
Process for the preparation of p-acetoxybenzyl chloride which comprises treating p-tolyl acetate with about 0.6 to 1.0 mole of chlorine per mole of p-tolyl acetate at a temperature of about 60° to 85° C. in the presence of (1) an effective amount of a halogenation-promoting free radical initiator, (2) at least one mole of acetic anhydride per mole of chlorine and (3) at least one mole of sodium acetate per mole of chlorine.
Claim 12
Dependent Claim
73 words
Process for the preparation of p-acetoxybenzyl chloride which comprises treating p-tolyl acetate with about 0.6 to 1.0 mole of chlorine per mole of p-tolyl acetate at a temperature of about 60° to 85° C. in the presence of (1) an effective amount of a halogenation-promoting free radical initiator, (2) at least one mole of acetic anhydride per mole of chlorine and (3) at least one mole of sodium acetate per mole of chlorine.
References Cited (Backward Citations)
US3226446A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-08-02 | 1986-02-01 | 1986-08-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-02 | 1990-02-01 | 1990-08-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-02 | 1994-02-01 | 1994-08-03 | $7700.00 | Window Closed / Lapsed |