(3-Methoxyphenyl)acetic acid → 3-Methoxyphenylacetyl chloride

HRID 542717Notes

Reaction equation

HRID 542717 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.S(Cl)([Cl:15])=O>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([Cl:15])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 15719(3-Methoxyphenyl)acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 27332463-Methoxyphenylacetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-methoxyphenylacetic acid (47.7 g, 0.287 m), thionyl chloride (50 ml) and N,N-dimethylformamide (6 drops) in toluene (500 ml) was stirred for 16 hours at 25° and concentrated in vacuo to afford 3-methoxyphenylacetyl chloride. The acetyl chloride was dissolved in chloroform (100 ml) and added to a solution of aminoacetaldehyde dimethyl acetal (32.1 g, 0.306 m) and triethylamine (32.4 g, 0.320 m) in chloroform (500 ml) stirred at 5°. The mixture was stirred at 25° for 16 hours, washed with water, 1.5N hydrochloric acid and water, dried with magnesium sulfate and concentrated in vacuo to give N-(2,2-dimethoxyethyl)-3-methoxybenzeneacetamide.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-274fa3cefcd8414ea086bfcb8a394784
Source dataset
uspto-grants-1987_04
Patent number
US04659706

Reaction notes

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