US4154757A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the manufacture of p-hydroxybenzyl cyanide
Assignee: Imperial Chemical Industries Ltd
•
Filing: 1978-05-22
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Granted: 1979-05-15
•
Expires: 1998-05-22
Abstract
Abstract A process for the manufacture of p-hydroxybenzyl cyanide which comprises reacting p-hydroxymandelic acid with cyanide ion. The product is a useful intermediate for the preparation of the β-adrenergic blocking agent atenolol.
Inventors
- 👤 Michael J. Cooper
- 👤 Philip N. Edwards
- 👤 Robert J. Copeland
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 10:55
CPC Classifications
C; C07; C07C; C07C255/00
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
31 words
A process for the manufacture of p-hydroxybenzyl cyanide which comprises reacting sodium or potassium p-hydroxymandelate with an alkali metal cyanide in a solvent at a temperature of up to 190° C.
Claim 2
Dependent Claim
31 words
A process for the manufacture of p-hydroxybenzyl cyanide which comprises reacting sodium or potassium p-hydroxymandelate with an alkali metal cyanide in a solvent at a temperature of up to 190° C.
Claim 3
Dependent Claim
15 words
A process as claimed in claim 1 wherein the alkali metal cyanide is sodium cyanide.
Claim 4
Dependent Claim
25 words
A process as claimed in claim 1 which is carried out in a dipolar, aprotic solvent at a temperature of between 120° and 190° C.
Claim 5
Dependent Claim
17 words
A process as claimed in claim 3 wherein the solvent is N,N-dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone or dimethyl sulphoxide.
Claim 6
Dependent Claim
17 words
A process as claimed in claim 4 which is carried out at a temperature of 135° C.
Claim 7
Dependent Claim
37 words
A process as claimed in claim 1 which is carried out in methanol or a mixture of methanol and 1,2-dimethoxyethane as solvent at the boiling point of the solvent and in the presence of a formate ester.
Claim 8
Dependent Claim
14 words
A process as claimed in claim 6 wherein the formate ester is methyl formate.
Claim 9
Dependent Claim
17 words
A process as claimed in claim 3 which is carried out in the presence of a base.
Claim 10
Dependent Claim
15 words
A process as claimed in claim 8 wherein the base is an alkali metal hydroxide.
Claim 11
Dependent Claim
17 words
A process as claimed in claim 6 which is carried out in the presence of a base.
Claim 12
Dependent Claim
21 words
A process as claimed in claim 10 wherein the reaction is carried out in the presence of an alkali metal carbonate.
Claim 13
Dependent Claim
20 words
A process as claimed in claim 1 wherein the sodium or potassium p-hydroxymandelate is in the form of its monohydrate.
References Cited (Backward Citations)
US3983160A
Cited
US3983151A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-14 | 1982-11-13 | 1983-05-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-14 | 1986-11-13 | 1987-05-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-14 | 1990-11-13 | 1991-05-15 | $7700.00 | Window Closed / Lapsed |