Reaction #310963

ord-0445cac1340449bb900981407bee45ad

Reaction equation

CCCCCCCCCCCCCCCCC(C(=O)O)c1ccccc1C
tolylstearic acid
CCCC
butane
CCC(C)=O
methylethyl ketone
O=O
O2
→
CCCCCCCCCCCCCCCCC(C(=O)O)(C(=O)O)c1ccccc1
Carboxyphenylstearic acid
Yield 47.9%

Reactants

CCCCCCCCCCCCCCCCC(C(=O)O)c1ccccc1C
tolylstearic acid
CCCC
butane
CCC(C)=O
methylethyl ketone
O=O
O2

Reagents

CC(=O)[O-].CC(=O)[O-].[Co+2]
cobalt (II) acetate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwere charged to the reactor

Procedure

The oxidation procedure of Example I was repeated except that only 40 gms cobalt (II) acetate was employed. Also, for this reaction 40 gms methylethyl ketone and 72 gms butane were charged to the reactor. Eighty percent conversion of the tolylstearic acid was achieved after only four hours reaction (105° C. and 350 psig O2). Carboxyphenylstearic acid was obtained in 47.9% yield.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04356315uspto-grants-1982_10