Phenylacetyl chloride → 2,3-Dichloro-4-phenylacetylanisole

HRID 1287514Notes

Reaction equation

HRID 1287514 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[O:13][CH3:14].[C:15]1([CH2:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(=S)=S>[Cl:12][C:11]1[C:6]([Cl:5])=[C:7]([O:13][CH3:14])[CH:8]=[CH:9][C:10]=1[C:22](=[O:23])[CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 161262,3-DichloroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 111301952,3-Dichloro-4-phenylacetylanisole

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
5 °C

Procedure

Aluminum chloride (395 g.) is added portionwise to a stirred solution of 2,3-dichloroanisole (500 g.) and phenylacetyl chloride (392 ml.) in carbon disulfide (1200 ml.) with cooling to 5°C. in an ice-water bath. After the addition, the reaction mixture is allowed to warm to room temperature, whereupon it forms a solid mass. After standing at 20°-25°C. overnight, the reaction vessel is flushed with nitrogen for 15 minutes, and crushed ice (about 2 kg.) and 12N HCl (400 ml.) are slowly added alternately with cooling in an ice bath. The pale yellow gummy solid that precipitates is collected by suction filtration on a sintered glass funnel to remove water as well as carbon disulfide. The solid product is washed well with water and sucked dry. To remove any persistent carbon disulfide, the product is triturated with hexane and again collected by filtration. Yield after drying in a steam oven at 70°C. for 18 hours is 803.5 g. (98%), mp 125°-127°C. A sample recrystallized from benzene-cyclohexane (2:1) melts at 128°-129°C.

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature, whereupon it
  3. customthe reaction vessel is flushed with nitrogen for 15 minutes
  4. customcrushed ice (about 2 kg.) and 12N HCl (400 ml.)
  5. additionare slowly added alternately
  6. temperaturewith cooling in an ice bath
  7. filtrationThe pale yellow gummy solid that precipitates is collected by suction filtration on a sintered glass funnel
  8. customto remove water as well as carbon disulfide
  9. washThe solid product is washed well with water
  10. customsucked dry
  11. customTo remove any persistent carbon disulfide
  12. customthe product is triturated with hexane
  13. filtrationagain collected by filtration
  14. customYield
  15. customafter drying in a steam oven at 70°C. for 18 hours
  16. customA sample recrystallized from benzene-cyclohexane (2:1) melts at 128°-129°C.

Sources & evidence

ORD record
ord-0688d885f7034f198c8e54fec5210b51
Source dataset
uspto-grants-1976_10
Patent number
US03984552

Reaction notes

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