Hydrochloric Acid → 1-(4-Chloro-2-methoxyphenyl)ethan-1-one

HRID 971640Notes

Reaction equation

N[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[ClH:13].N([O-])=O.[Na+]>[Cu]Cl.O.C(O)(=O)C>[Cl:13][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred and cooled (0° C.) solution of 30 parts of 1-(4-amino-2-methoxyphenyl)ethanone in 360 parts of a concentrated hydrochloric acid solution, 75 parts of water and 30 parts of acetic acid is diazotated with a solution of 17.25 parts of sodium nitrite in 200 parts of water. After stirring for 30 minutes at 0° C., the whole is poured onto a solution of 30 parts of copper (I) chloride in 240 parts of a concentrated hydrochloric acid solution while stirring. The mixture is heated for 1 hour at 60° C. After cooling to room temperature, the product is extracted twice with 2,2'-oxybispropane. The combined extracts are washed successively with water, a diluted sodium hydroxide solution and again twice with water, dried, filtered and evaporated, yielding 28 parts (76%) of 1-(4-chloro-2-methoxyphenyl)ethanone; mp. 55° C.

Workup

stirringAfter stirring for 30 minutes at 0° C.
stirringwhile stirring
temperatureAfter cooling to room temperature
extractionthe product is extracted twice with 2,2'-oxybispropane
washThe combined extracts are washed successively with water
dry with materiala diluted sodium hydroxide solution and again twice with water, dried
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-a1e277808a2e45d1a5cc76d7929b3341
Source dataset: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04160838

Reaction notes

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