US4562280A
Expired / Lapsed
US
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Chloromethylation of deactivated aromatic compounds
Assignee: Dow Chemical Co
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Filing: 1984-10-18
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Granted: 1985-12-31
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Expires: 2004-10-18
Abstract
Abstract The invention is a process for the chloromethylation of an aromatic compound, substituted with an alkyl group and a deactivating moiety, which comprises contacting an aromatic compound, substituted with an alkyl group and a deactivating group, with a chloromethyl alkyl ether in the presence of a catalytic amount of ferric chloride or stannic chloride, under conditions such that an aromatic compound, substituted with an alkyl group, a chloromethyl group, and a deactivating group, wherein the alkyl and chloromethyl groups are on adjacent carbon atoms, is prepared.
Inventors
- 👤 Jo Ann Gilpin
- 👤 Lowell B. Lindy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 21:01
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/76; C07C69/78
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
83 words
A process for the chloromethylation of an aromatic compound, substituted with an alkyl group and a deactivating moiety, which comprises contacting an aromatic compound, substituted with an alkyl group and a deactivating group, with a chloromethyl alkyl ether in the presence of a catalytic amount of ferric chloride or stannic chloride, under conditions such that an aromatic compound, substituted with an alkyl group, a chloromethyl group, and a deactivating group, wherein the alkyl and chloromethyl groups are on adjacent carbon atoms, is prepared.
Claim 2
Dependent Claim
83 words
A process for the chloromethylation of an aromatic compound, substituted with an alkyl group and a deactivating moiety, which comprises contacting an aromatic compound, substituted with an alkyl group and a deactivating group, with a chloromethyl alkyl ether in the presence of a catalytic amount of ferric chloride or stannic chloride, under conditions such that an aromatic compound, substituted with an alkyl group, a chloromethyl group, and a deactivating group, wherein the alkyl and chloromethyl groups are on adjacent carbon atoms, is prepared.
Claim 3
Dependent Claim
15 words
The process of claim 1 wherein the contacting occurs in an inert organic reaction media.
Claim 4
Dependent Claim
40 words
The process of claim 2 wherein the contacting occurs in the presence of a reaction promoter comprising SOCl 2 , SiCl 4 , TiCl 4 , PCl 3 , SO 2 Cl 2 , PCl 5 or ClSO 3 H.
Claim 5
Dependent Claim
104 words
The process of claim 3 wherein the aromatic compound substituted with an alkyl group and a deactivating group corresponds to the formula R.sup.1 --Ar--R.sup.2 the aromatic compound substituted with an alkyl group, chloromethyl group and a deactivating group, wherein the alkyl and chloromethyl groups are on adjacent carbon atoms corresponds to the formula ##STR8## and the chloromethylalkyl ether corresponds to the formula ClCH.sub.2 OR.sup.3 wherein Ar is an aromatic radical; R 1 is a C 1-10 lower alkyl group; R 2 is a hydrocarbyloxycarbonyl, a hydrocarbylamido, hydrocarbylcarbonyl, carboxyl, carbonylhalo, nitro, sulfone or sulfoxide; and R 3 is C 1-10 alkyl or C 3-10 haloalkyl.
Claim 6
Dependent Claim
39 words
The process of claim 4 wherein at least about 2 percent by weight based on the aromatic compound of the catalyst, and at least about 10 percent by weight based on the aromatic compound of the promoter are present.
Claim 7
Dependent Claim
48 words
The process of claim 5 wherein the catalyst is present in an amount of between about 5 and 60 percent by weight of the aromatic compound, and the promoter is present in an amount of between about 10 and 80 percent by weight based on the aromatic compound.
Claim 8
Dependent Claim
26 words
The process of claim 6 wherein the promoter is SOCl 2 , SiCl 4 , TiCl 4 , PCl 3 or SO 2 Cl 2 .
Claim 9
Dependent Claim
12 words
The process of claim 7 wherein the promoter is SOCl 2 .
Claim 10
Dependent Claim
12 words
The process of claim 8 wherein the catalyst is FeCl 3 .
Claim 11
Dependent Claim
48 words
The process of claim 9 wherein Ar is a benzene, naphthalene, phenanthrene, anthracene, a biaryl moiety, or two or more aromatic radicals bridged by alkylene or cycloalkylene moieties; R 1 is C 1-4 alkyl; R 2 is hydrocarbyloxycarbonyl, hydrocarbylamido or nitro; and R 3 is C 1-4 alkyl.
Claim 12
Dependent Claim
25 words
The process of claim 10 wherein Ar is benzene, naphthalene, biphenyl, binaphthyl, diphenylalkane or diphenyl cycloalkane radical; and R 2 is alkoxy carbonyl or alkylamido.
Claim 13
Dependent Claim
23 words
The process of claim 11 wherein Ar is benzene; R 1 is methyl; R 2 is alkoxy carbonyl; and R 3 is methyhl.
Claim 14
Dependent Claim
20 words
The process of claim 11 wherein the inert reaction media is carbon disulfide, aliphatic hydrocarbon or a chlorinated aliphatic hydrocarbon.
Claim 15
Dependent Claim
16 words
The process of claim 13 wherein the temperature is between about 40° C. and 80° C.
Claim 16
Dependent Claim
54 words
A process for the chloromethylation of an alkyl alkylbenzoate wherein the alkyl alkylbenzoate is contacted with chloromethyl methyl ether in a chlorinated hydrocarbon or carbon disulfide reaction medium in the presence of a catalytic amount of FeCl 3 and a reaction promoter comprising SOCl 2 under conditions such that an alkyl 1-alkyl-2-chloromethylbenzoate is prepared.
Claim 17
Dependent Claim
54 words
A process for the chloromethylation of an alkyl alkylbenzoate wherein the alkyl alkylbenzoate is contacted with chloromethyl methyl ether in a chlorinated hydrocarbon or carbon disulfide reaction medium in the presence of a catalytic amount of FeCl 3 and a reaction promoter comprising SOCl 2 under conditions such that an alkyl 1-alkyl-2-chloromethylbenzoate is prepared.
Claim 18
Dependent Claim
33 words
The process of claim 14 wherein the alkyl alkylbenzoate corresponds to the formula ##STR9## and the alkyl 1-alkyl-2-chloromethylbenzoate corresponds to the formula ##STR10## wherein R 1 and R 4 are C 1-10 alkyl.
References Cited (Backward Citations)
US1879912A
Cited
US1972956A
Cited
US2219873A
Cited
US2402847A
Cited
US2361355A
Cited
US2361065A
Cited
US2436151A
Cited
US2423530A
Cited
US2882325A
Cited
GB925627A
Cited
US4070366A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1988-12-30 | 1989-07-01 | 1989-12-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-30 | 1993-07-01 | 1993-12-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-30 | 1997-07-01 | 1997-12-31 | $7700.00 | Window Closed / Lapsed |