Dichloromethane → 1-(3-Chloro-4-hydroxyphenyl)ethanone

HRID 1252581Notes

Reaction equation

HRID 1252581 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(Cl)[Cl:12]>>[CH3:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([Cl:12])[CH:4]=1)=[O:10]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 74694'-Hydroxyacetophenone

Product 1

HCID 10515141-(3-Chloro-4-hydroxyphenyl)ethanone

Procedure

50 gm of p-hydroxyacetophenone were dissolved in 500 ml of hot methylene dichloride and filtered through a small pad of silica gel. The solution was allowed to cool and the methylene dichloride was stripped off to obtain 41.75 gm (0.31 mol) of crystals. These crystals were dissolved in about 1.5 liters of methylene dichloride. The reaction flask was placed in an ice bath and chlorine gas was bubbled through the solution. After about a total of 5 minutes of Cl2(g) bubbling, the methylene chloride was stripped off to yield more than 30 gm of white crystals (>90% pure) of 3-chloro-4-hydroxy acetophenone.

Workup

  1. filtrationfiltered through a small pad of silica gel
  2. temperatureto cool

Sources & evidence

ORD record
ord-a313f466b8b24abb862cdbfb83cf8ee7
Source dataset
uspto-grants-1988_05
Patent number
US04743703

Reaction notes

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