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US4603227A
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Novel process for preparing α-(trichloromethyl)benzyl alcohols from benzaldehydes
Assignee: Merck and Co Inc
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Filing: 1985-09-25
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Granted: 1986-07-29
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Expires: 2005-09-25
Abstract
Abstract This invention relates to a novel and improved process for preparing alpha -(trichloromethyl) benzyl alcohols, particularly, trichloromethyl-3-nitrobenzyl alcohol a key intermediate useful in the preparation of clorsulon (4-amino-6-(trichloroethenyl)-1,3-benzene-disulfonamide) via a base-catalyzed condensation reaction of benzaldehydes and chloroform.
Inventors
- 👤 George G. Hazen
- 👤 Jean M. Wyvratt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 16:14
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/64; C07C201/00; C07C201/06; C07C201/12; C07C41/00; C07C41/01; C07C41/18; C07C41/30
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
69 words
A process for preparing α-(trichloromethyl)benzyl alcohols of the formula ##STR2## wherein R 1 is hydrogen, alkoxy (C 1 -C 6 ), nitro, alkyl(C 1 -C 6 ), halogen, amino, aryl(C 6 -C 9 ) or aralkyl (C 7 -C 12 ) which comprises condensing a benzaldehyde compound with chloroform in the presence of a dipolar-aprotic solvent and a base in an alkanol at a sub-zero to zero degree temperature.
Claim 2
Dependent Claim
69 words
A process for preparing α-(trichloromethyl)benzyl alcohols of the formula ##STR2## wherein R 1 is hydrogen, alkoxy (C 1 -C 6 ), nitro, alkyl(C 1 -C 6 ), halogen, amino, aryl(C 6 -C 9 ) or aralkyl (C 7 -C 12 ) which comprises condensing a benzaldehyde compound with chloroform in the presence of a dipolar-aprotic solvent and a base in an alkanol at a sub-zero to zero degree temperature.
Claim 3
Dependent Claim
77 words
The process of claim 1, wherein said benzaldehyde compound is selected from the group consisting of 3-nitrobenzaldehyde, benzaldehyde and 4-anisaldehyde; said dipolar-aprotic solvent is selected from the group consisting of dimethylformamide, N-methylpyrrolidinone and N-ethylpyrrolidinone; said base is selected from the group consisting of sodium hydroxide, potassium t-butoxide, calcium hydroxide, sodium methoxide and potassium hydroxide; and said alkanol is selected from the group consisting of methanol, ethanol and isopropanol at temperature ranging from -25° C. to 0° C.
Claim 4
Dependent Claim
32 words
The process of claim 2, wherein said compound is 3-nitrobenzaldehyde, said solvent is dimethylformamide, said base is potassium hydroxide and said alkanol is methanol at temperatures ranging from -15° to 0° C.
Claim 5
Dependent Claim
11 words
The process of claim 3, wherein said temperature is -9° C.
Claim 6
Dependent Claim
32 words
The process of claim 2, wherein said compound is benzaldehyde, said solvent is N-methylpyrrolidinone, said base is potassium hydroxide and said alkanol methanol at temperature ranging from -15° C. to 0° C.
Claim 7
Dependent Claim
11 words
The process of claim 5, wherein the temperature is -5° C.
Claim 8
Dependent Claim
33 words
The process of claim 2, wherein said compound is 3-nitrobenzaldehyde, said solvent is N-methylpyrrolidinone, said base is potassium hydroxide and said alkanol is methanol at temperatures ranging from -15° C. to 0° C.
Claim 9
Dependent Claim
11 words
The process of claim 7, wherein said temperature is -5° C.
Claim 10
Dependent Claim
33 words
The process of claim 2, wherein said compound in anisaldehyde, said solvent is N-ethylpyrrolidinone, said base is potassium t-butoxide and said alkanol is methanol at temperatures ranging from -15° C. to 0° C.
Claim 11
Dependent Claim
11 words
The process of claim 9, wherein the temperature is -10° C.
Claim 12
Dependent Claim
12 words
The process of claim 3, wherein said alkanol is ethanol or isopropanol.
Claim 13
Dependent Claim
10 words
The process of claim 11, wherein said alkanol is isopropanol.
References Cited (Backward Citations)
US3419623A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-07-28 | 1990-01-27 | 1990-07-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-07-28 | 1994-01-27 | 1994-07-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-07-28 | 1998-01-27 | 1998-07-29 | $7700.00 | Window Closed / Lapsed |