Phenylacetic Acid → Tert-butyl 2-phenylacetate

HRID 1706278Notes

Reaction equation

HRID 1706278 reaction equation
[I-].BrC1C=CC=C[N+]=1C.[C:10]([OH:14])([CH3:13])([CH3:12])[CH3:11].[C:15]1([CH2:21][C:22](O)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:15]1([CH2:21][C:22]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 999Phenylacetic AcidHCID 6386tert-ButanolHCID 7622TributylamineHCID 122339072-Bromo-1-methylpyridinium iodide

Product 1

HCID 316203Tert-butyl 2-phenylacetateYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspended toluene (2 ml) solution of 2-bromo-1-methylpyridinium iodide (720 mg, 2.4 mmol) was added a mixture of tert-butyl alcohol (148 mg, 2.0 mmol), phenylacetic acid (272 mg, 2.0 mmol) and tri-n-butylamine (888 mg, 4.8 mmol) in toluene (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 tert-butyl phenylacetate was isolated in 82% 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-40861ae4ef2e47d1a35704b3401ce8bc
Source dataset
uspto-grants-1980_06
Patent number
US04206310

Reaction notes

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