Methanol → Methyl phenylacetate

HRID 2295404Notes

Reaction equation

HRID 2295404 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O-:10].[Na+].[CH3:12][OH:13]>>[C:2]1([CH2:1][C:9]([O:13][CH3:12])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 7503Benzyl ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 7559Methyl phenylacetateYield 85%

Procedure

110 g (0.87 mole) of benzyl chloride and, simultaneously but separately, a solution of 46 g (0.85 mole) of sodium methylate in 130 g of methanol, were added gradually in the course of one hour, with vigorous stirring, to a solution of 160 g of methanol and 10 g of K[Fe(CO)3NO] (0.048 mole) under a carbon monoxide pressure of 1.7 bars, at 55° C. The reaction was complete after a further two hours. Conventional working up gave methyl phenylacetate in 85% yield.

Workup

  1. customat 55° C

Sources & evidence

ORD record
ord-9bd2a61d937045878dd3e92d262ef336
Source dataset
uspto-grants-1984_01
Patent number
US04424394

Reaction notes

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