Process for the synthesis of acetic acid, (dimethoxyphosphinyl) [[1,1-dimethylethyl)dimethylsilyl]-oxy]-, (4-nitrophenyl) methyl ester

• US 5,288,888 A
• Filed: 04/28/1993
• Issued: 02/22/1994
• Est. Priority Date: 04/28/1993
• Status: Expired due to Fees

• Current Assignee: American Colloid Company (Minerals Technologies Incorporated)
• Original Assignee: American Colloid Company (Minerals Technologies Incorporated)
• Inventors: Green, Kenneth E., Feigelson, Gregg B., Jurgens, Alex R., Ruso, Edward R., Jennings, Mellard N., Blum, David M.
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US08/053,283
• Time in Patent Office: 300 Days
• Field of Search: 556/405
• US Class Current: 556/405
• CPC Class Codes: C07C 201/12 by reactions not involving the formation of nitro groups
• CPC Class Codes: C07C 205/42 having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
• CPC Class Codes: C07F 9/4006 Esters of acyclic acids which can have further substituents on alkyl

Abstract

The invention is an improved process for the large scale production of acetic acid, (dimethoxyphosphinyl) [[1,1-dimethylethyl)dimethylsilyl]oxy]-, (4-nitrophenyl)methyl ester.

Claims

1. A process for the preparation of a compound of the formula:

##STR3## which comprises the steps of (a) reaction of L-tartaric acid of the formula;

##STR4## with p-nitrobenzylbromide in the presence of an amine in a solvent to the corresponding bis-(4-nitrophenyl)-ester of the formula;

##STR5## (b) oxidizing the bis-(4-nitrophenyl)ester with an oxidant in a solvent to product the dihydroxyacetic acid 4-nitrophenyl ester of the formula;

##STR6## (c) reacting the dihydroxyacetic acid 4-nitrophenyl ester with dimethylphosphite in a solvent to produce the dimethoxyphosphinyl compound of the formula;

##STR7## (d) reacting the dimethoxyphosphinyl compound with t-butyldimethylsilyl chloride in a solvent in the presence of a base to afford the desired compound of the formula;

##STR8##

2. A process according to claim 1, wherein the solvent of step (a) is N,N-dimethylformamide.

3. A process according to claim 2, wherein the amine of step (a) is triethylamine.

4. A process according to claim 3, wherein the oxidant of step (b) is periodic acid.

5. A process according to claim 4, wherein the solvent of step (b) is tetrahydrofuran.

6. A process according to claim 5, wherein the solvent of step (c)is ethyl acetate.

7. A process according to claim 6, wherein the solvent of step (d) is N,N-dimethylformamide.

8. A process according to claim 7, wherein the base of step (d) is imidazole.