Benzyl Alcohol → Benzyl 2-bromopropanoate

HRID 223420

Reaction equation

HRID 223420 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[CH2:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>C(OCC)C>[Br:1][CH:2]([CH3:6])[C:3]([O:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 962WaterHCID 979802-Bromopropanoyl chloride

Product 1

HCID 298874Benzyl 2-bromopropanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Bromopropionyl chloride (213.4 g) was added dropwise to benzyl alcohol (145.8 g) with stirring under a stream of nitrogen, keeping the temperature of the reaction mixture below 30° C. by cooling with cold water. When all the acid chloride has been added, the mixture was stirred for another two hours at ambient temperature. The reaction mixture was then diluted with diethyl ether (200 ml) and washed with water until free of acid. The ethereal solution was dried and evaporated and the residue distilled to give benzyl 2-bromopropionate, b.p. 82°-85°/0.5 Torr.

Workup

  1. customthe temperature of the reaction mixture below 30° C.
  2. stirringthe mixture was stirred for another two hours at ambient temperature
  3. washwashed with water until free of acid
  4. customThe ethereal solution was dried
  5. customevaporated
  6. distillationthe residue distilled

Sources & evidence

ORD record
ord-1c00f06cea1740ed92e24c97ab00991d
Source dataset
uspto-grants-1982_10
Patent number
US04354034

Linked notes

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