US4014940A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing m-phenoxybenzylalcohol and side-chain halogenated m-phenoxytoluene
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1974-01-18
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Granted: 1977-03-29
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Expires: 1994-01-18
Abstract
Abstract A process for preparing m-phenoxybenzyl, m-phenoxybenzal halides or a mixture thereof comprising halogenating m-phenoxytoluene in the presence of a phosphorus halide in the high temperature region above 220° C, and a process for preparing m-phenoxybenzylalcohol comprising halogenating m-phenoxytoluene as above, reacting the resulting side-chain halogenated m-phenoxytoluene with an alkali metal salt of acetic acid and then (a) reducing and hydrolyzing the resulting m-phenoxybenzylacetate and m-phenoxybenzaldehyde, or (b) reducing the resulting m-phenoxybenzylacetate and m-phenoxybenzaldehyde, reacting the resulting product with acetic anhydride and an alkali metal salt of acetic acid and hydrolyzing the resulting m-phenoxybenzylacetate are disclosed.
Inventors
- 👤 Yoshitaka Ume
- 👤 Takashi Matsuo
- 👤 Nobushige Itaya
- 👤 Nobuo Ohno
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:27
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/42; C07C41/00; C07C41/01; C07C41/18; C07C41/22; C07C41/26; C07C45/43
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
33 words
A process for preparing m-phenoxybenzyl, m-phenoxybenzal halides or a mixture thereof which comprises halogenating m-phenoxytoluene with a halogen in the presence of a phosphorus halide in the high temperature region above 220° C.
Claim 2
Dependent Claim
33 words
A process for preparing m-phenoxybenzyl, m-phenoxybenzal halides or a mixture thereof which comprises halogenating m-phenoxytoluene with a halogen in the presence of a phosphorus halide in the high temperature region above 220° C.
Claim 3
Dependent Claim
56 words
A process for preparing m-phenoxybenzylalcohol represented by the formula, ##STR8## which comprises halogenating m-phenoxytoluene with a halogen in the presence of a phosphorus halide in the high temperature region above 220° C, reacting the resulting side chain-halogenated m-phenoxytoluene with an alkali metal salt of acetic acid, and then reducing and hydrolyzing the resulting m-phenoxybenzylacetate and m-phenoxybenzaldehyde.
Claim 4
Dependent Claim
56 words
A process for preparing m-phenoxybenzylalcohol represented by the formula, ##STR8## which comprises halogenating m-phenoxytoluene with a halogen in the presence of a phosphorus halide in the high temperature region above 220° C, reacting the resulting side chain-halogenated m-phenoxytoluene with an alkali metal salt of acetic acid, and then reducing and hydrolyzing the resulting m-phenoxybenzylacetate and m-phenoxybenzaldehyde.
Claim 5
Dependent Claim
16 words
The process according to claim 1, wherein said phosphorus halide is phosphorus trichloride or phosphorus pentachloride.
Claim 6
Dependent Claim
19 words
The process according to claim 1, wherein the molar ratio of phosphorus polyhalide to m-phenoxytoluene is 1/10 to 1/30.
Claim 7
Dependent Claim
20 words
The process according to claim 2, wherein the alkali metal salt of acetic acid is sodium acetate or potassium acetate.
Claim 8
Dependent Claim
21 words
The process according to claim 2, wherein said reducing is carried out in the presence of sodium borohydride at room temperature.
Claim 9
Dependent Claim
23 words
The process according to claim 2, wherein said reducing and hydrolyzing is carried out under the conditions of Cannizzaro-reaction with alkali and formaldehyde.
Claim 10
Dependent Claim
23 words
The process according to claim 2, wherein said reducing is carried out by catalytic hydrogenation in the presence of Raney nickel or palladium.
Claim 11
Dependent Claim
25 words
The process according to claim 2, wherein said reaction with an alkali metal salt of acetic acid is conducted from room temperature to 200° C.
References Cited (Backward Citations)
US1733268A
Cited
US2765346A
Cited
US2231026A
Cited
US3068296A
Cited
US3280199A
Cited
US3859364A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-28 | 1980-09-27 | 1981-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-28 | 1984-09-27 | 1985-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-28 | 1988-09-27 | 1989-03-29 | $7700.00 | Window Closed / Lapsed |