(3,4-Dimethoxyphenyl)acetic acid → (3,4-Dimethoxyphenyl)acetyl chloride

HRID 371064

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].S(Cl)([Cl:17])=O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([Cl:17])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 20 g. (0.10 mole) of 3,4-dimethoxyphenylacetic acid in 100 ml. of benzene was added dropwise 70 ml. (115 g., 0.98 mole) of thionyl chloride. The solution was heated to 50° C. for two hours, then evaporated in vacuo to give a residue of 3,4-dimethoxyphenylacetyl chloride. A solution of 21.4 g. (0.10 mole) of the acid chloride in 70 ml. of chloroform was added with stirring to a solution of 70 ml. of chloroform and 22.2 ml. (30.0 g., 0.30 mole) of N,N-di-(n-propyl)amine at 0° C. The resulting mixture was heated at 50° C. for two hours, cooled, diluted and washed with dilute hydrochloric acid, dilute sodium carbonate solution and water. The dried chloroform solution was evaporated in vacuo to give N,N-di(n-propyl)-3,4-dimethoxyphenylacetamide.

Workup

customevaporated in vacuo

Sources & evidence

ORD record: ord-8d0f0ea6732e40e4b7790e8bd958d1e3
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04529604

Linked notes

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