Methyl phenylacetate → Ethyl phenylacetate

HRID 2288947Notes

Reaction equation

HRID 2288947 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Li+].[Br-].[CH2:14]1CCN2C(=NCCC2)CC1>C(O)C>[CH2:1]([O:2][C:3](=[O:11])[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH3:14]

Participants

5

Reactant 3

HCID 7559Methyl phenylacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82050Lithium Bromide

Product 1

HCID 7590Ethyl phenylacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following method A, phenylacetic acid methyl ester (4.51 g, 30 mmol) and LiBr (13.03 g, 150 mmol) were dissolved in ethanol (150 ml). DBU (2.28 g, 15 mmol) was added and the reaction mixture was agitated at room temperature for an hour. It was then hydrolysed and processed as described. Vacuum distillation yielded 4.40 g (90% of the theoretical yield) of pure phenylacetic acid ethyl ester, b.p. 65.5-66° C./l Torr.

Workup

  1. distillationVacuum distillation
  2. customyielded 4.40 g (90% of the

Sources & evidence

ORD record
ord-9e1c166161da4d9989f333d6436681d9
Source dataset
uspto-grants-2000_07
Patent number
US06090913

Reaction notes

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