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

HRID 1940831Notes

Reaction equation

HRID 1940831 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

4

Reactant 2

HCID 117685733,4,4-Trifluorobut-3-en-1-olHCID 131709961Jones' reagent

Product 1

HCID 152391743,4,4-Trifluoro-3-butenoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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-trifluoro-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. ##STR3##

Workup

  1. customare at a temperature of about 51°-54° C

Sources & evidence

ORD record
ord-ebf28d1a1b0e4f96993cd360946b9e6d
Source dataset
uspto-grants-1997_12
Patent number
US05700840

Reaction notes

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