Sulfuric Acid → 4'-Chloro-2-phenylacetophenone

HRID 1659552Notes

Reaction equation

HRID 1659552 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](N)=[O:16])=[CH:13][CH:12]=1.S(=O)(=O)(O)O>CCOCC>[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:16])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7503Benzyl ChlorideHCID 120844-ChlorobenzamideHCID 5462224Magnesium

Product 1

HCID 2338404'-Chloro-2-phenylacetophenone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

50.6 g of dry benzyl chloride in 200 ml of dry ether was treated with 10 g of magnesium. When the reaction was complete, 15.6 g of 4-chlorobenzamide was added in portions with stirring. When the addition was complete the mixture was stirred and refluxed for 65 hours. The cooled mixture then was poured onto 400 g of ice containing 40 g of concentrated sulphuric acid. Several extractions with ether yielded the crude product as a white solid. Recrystallization from methylated spirit gave white crystals of 4-chlorodeoxybenzoin, 1A, mp: 106°-106.5° C.

Workup

  1. additionWhen the addition
  2. stirringwas stirred
  3. temperaturerefluxed for 65 hours
  4. extractionSeveral extractions with ether
  5. customyielded the crude product as a white solid
  6. customRecrystallization from methylated spirit

Sources & evidence

ORD record
ord-0d0e45c207b24aef8036320fce36197f
Source dataset
uspto-grants-1981_12
Patent number
US04304789

Reaction notes

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