US4304940A
Expired / Lapsed
US
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Preparation of 2-alkyl- and 2-aryl-thiomethylphenols
Assignee: Bayer AG
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Filing: 1980-08-27
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Granted: 1981-12-08
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Expires: 2000-08-27
Abstract
Abstract In the preparation of a 1-alkyl- and 2-aryl-thio-methylphenol of the formula ##STR1## in which R 1 is, or the radicals R 1 are, in the 3-, 5- and/or 6-positions relative to the hydroxyl group and each independently is a hydrogen or halogen atom, or an alkyl, cycloalkyl, aryl, aralkyl or alkoxy group, n is 1, 2, or 3, and R 2 is an optionally substituted alkyl group having 1 to 12 carbon atoms, an optionally substituted cycloalkyl group having 3 to 6 carbon atoms, an optionally substituted phenyl radical or an optionally substituted aralkyl radical, by reacting a phenol of the formula ##STR2## with formaldehyde or an formaldehyde producing compound and with a mercaptan or a thiophenol of the formula R.sup.2 --S--H. the improvement which comprises effecting the reaction at a temperature of about 90° to 220° C. in the presence of at least one compound of lithium, magnesium, calcium, strontium, barium, zinc, cadmium, lead, manganese, cobalt, nickel, cooper, iron, chromium and aluminum as a catalyst. The products are obtained in high yield and selectivity.
Inventors
- 👤 Karlfried Wedemeyer
- 👤 Helmut Fiege
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 23:21
CPC Classifications
C; C07; C07C; C07C323/00
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
188 words
In the preparation of a 2-alkyl- and 2-aryl-thiomethylphenol of the formula ##STR7## in which R 1 is, or the radicals R 1 are, in the 3-, 5- and/or 6-positions relative to the hydroxyl group and each independently is a hydrogen or halogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a phenyl, benzyl or C 1 to C 4 -alkoxy radical, n is 1, 2, or 3, and R 2 is an alkyl group having 1 to 12 carbon atoms, an alkoxy-substituted alkyl group, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl or benzyl group or an alkyl- and/or halogen-substituted phenyl group, by reacting a phenol or the formula ##STR8## with formaldehyde or a formaldehyde producing compound and with a mercaptan or a thiophenol of the formula R.sup.2 --S--H, the improvement which comprises effecting the reaction at a temperature of about 90° to 220° C. in the presence of at least one compound of lithium, magnesium, calcium, strontium, barium, zinc, cadmium, lead, manganese, cobalt, nickel, copper, iron, chromium and aluminum as a catalyst.
Claim 2
Dependent Claim
188 words
In the preparation of a 2-alkyl- and 2-aryl-thiomethylphenol of the formula ##STR7## in which R 1 is, or the radicals R 1 are, in the 3-, 5- and/or 6-positions relative to the hydroxyl group and each independently is a hydrogen or halogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a phenyl, benzyl or C 1 to C 4 -alkoxy radical, n is 1, 2, or 3, and R 2 is an alkyl group having 1 to 12 carbon atoms, an alkoxy-substituted alkyl group, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl or benzyl group or an alkyl- and/or halogen-substituted phenyl group, by reacting a phenol or the formula ##STR8## with formaldehyde or a formaldehyde producing compound and with a mercaptan or a thiophenol of the formula R.sup.2 --S--H, the improvement which comprises effecting the reaction at a temperature of about 90° to 220° C. in the presence of at least one compound of lithium, magnesium, calcium, strontium, barium, zinc, cadmium, lead, manganese, cobalt, nickel, copper, iron, chromium and aluminum as a catalyst.
Claim 3
Dependent Claim
29 words
A process according to claim 1, wherein the reaction is carried out in the presence of about 0.1 to 5×10 -6 mole of catalyst compound per mole of phenol.
Claim 4
Dependent Claim
30 words
A process according to claim 1, wherein the reaction is carried out in the presence of about 1×10 -2 to 1×10 -5 mole of catalyst compound per mole of phenol.
Claim 5
Dependent Claim
26 words
A process according to claim 1, wherein the catalyst comprises at least one compound of lithium, magnesium, calcium, strontium, barium, zinc, cadmium, manganese, lead and cobalt.
Claim 6
Dependent Claim
10 words
A process according to claim 1, wherein n is 1.
Claim 7
Dependent Claim
13 words
A process according to claim 5, wherein R 1 is a hydrogen atom.
Claim 8
Dependent Claim
17 words
A process according to claim 1, wherein the reaction is effected at about 100° to 200° C.
Claim 9
Dependent Claim
46 words
A process according to claim 3, wherein the catalyst comprises at least one compound of lithium, magnesium, calcium, strontium, barium, zinc, cadmium, manganese, lead and cobalt, R 1 is a hydrogen atom, n is 1, and the reaction is effected at about 100° to 200° C.
Claim 10
Dependent Claim
30 words
A process according to claim 1, wherein the catalyst comprises at least one compound of magnesium, calcium, strontium, barium, zinc, cadmium, lead, manganese, cobalt, nickel, copper, iron, chromium or aluminum.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-12-07 | 1985-06-08 | 1985-12-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-12-07 | 1989-06-08 | 1989-12-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-12-07 | 1993-06-08 | 1993-12-08 | $7700.00 | Window Closed / Lapsed |