Benzyl Alcohol → 3,4,4-Trifluoro-3-butenoic acid, phenylmethyl ester

HRID 2210201Notes

Reaction equation

HRID 2210201 reaction equation
[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4](Cl)=[O:5].[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl>[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5]

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 109207893,4,4-Trifluoro-3-butenoyl chloride

Product 1

HCID 152391893,4,4-Trifluoro-3-butenoic acid, phenylmethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3,4,4-trifluoro-3-butenoyl chloride (2.8 g, 0.0176 mole) and benzyl alcohol (0.9 g, 0.0083 mole) in 20 mL dichloromethane is heated at reflux for 40 h. The solution is cooled to room temperature, diluted with dichloromethane (15 mL), washed successively with 5% sodium bicarbonate, water and brine, and dried. Evaporation of the solvent gave 1.75 g of analytically pure product as a pale yellow oil, a 92% yield.

Workup

  1. temperatureat reflux for 40 h
  2. washwashed successively with 5% sodium bicarbonate, water and brine
  3. customdried
  4. customEvaporation of the solvent
  5. customgave 1.75 g of analytically pure product as a pale yellow oil

Sources & evidence

ORD record
ord-d1c7bdc615234d8abe2a3fe654a51f12
Source dataset
uspto-grants-1995_10
Patent number
US05457134

Reaction notes

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