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

HRID 54732

Reaction equation

HRID 54732 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-33802d7b13274c35bbbf39266a33b36e
Source dataset
uspto-grants-1997_04
Patent number
US05623084

Linked notes

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