3,4,4-Trifluorobut-3-en-1-ol → 3,4,4-Trifluoro-3-butenoic acid

Reaction equation

[F:1][C:2](=[C:6]([F:8])[F:7])[CH2:3][CH2:4][OH:5].CC(C)=[O:11].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[F:1][C:2](=[C:6]([F:8])[F:7])[CH2:3][C:4]([OH:11])=[O:5]

Participants

Procedure

The first method involves hydrolysis of 4-bromo-1,1,2-trifluoro- 1-butene (II) with water in the presence of N-methyl pyrrolidinone to give 3,4,4-trifluor-3-buten-1-ol (III), followed by Jones oxidation under conditions not previously known. These conditions are at a temperature of about 51°-54° C. In addition, the 3,4,4-trifluoro-3-buten-1-ol in acetone solvent and the Jones reagent are added to the reaction vessel simultaneously to afford 3,4,4-trifluoro-3-butenoic (IV) acid in 52% overall yield. ##STR4##