Benzyl Alcohol → Benzyl phenylacetate

HRID 1706277Notes

Reaction equation

HRID 1706277 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:18]1([CH2:24][C:25](O)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C(C)=CC=CC=1C>C(Cl)Cl>[C:18]1([CH2:24][C:25]([O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 999Phenylacetic AcidHCID 79372,6-LutidineHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 60999Benzyl phenylacetateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspended CH2Cl2 (2 ml) solution of 2-chloro-1-methylpyridinium iodide (306 mg, 1.2 mmol) was added a mixture of benzyl alcohol (108 mg, 1.0 mmol), phenylacetic acid (136 mg, 1.0 mmol) and 2,6-lutidine (257 mg, 2.4 mmol) in CH2Cl2 (2 ml), and the resulting mixture was refluxed for 3 hours. After evaporation of the solvent, the residue was separated by silica gel column chromatography, and benzyl phenylacetate was isolated in 98% yield.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hours
  2. customAfter evaporation of the solvent
  3. customthe residue was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-9e95b9d097fe416d8186401d93eb7461
Source dataset
uspto-grants-1980_06
Patent number
US04206310

Reaction notes

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