Phenylacetyl chloride → HCID 53927873, compound

HRID 1447665Notes

Reaction equation

HRID 1447665 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[C:11]1([CH2:17][C:18](Cl)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:18](=[O:19])[CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

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

Product 1

HCID 53927873HCID 53927873, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a stirred mixture of 2,3-dichloroanisole (62 g., 0.35 mole), phenylacetyl chloride (54 g., 0.35 mole) and carbon disulfide (250 ml.) is added portionwise aluminum chloride (47 g., 0.35 mole) with cooling at 0°-5° C. The reaction mixture is left at 25° C. for 17 hours, the carbon disulfide removed, and the residue treated with ice-water and concentrated hydrochloric acid (50 ml.) to give 68.8 g. of 2,3-dichloro-5-phenylacetylanisole which melts at 126°-129° C. on crystallization from benzene:cyclohexane, 2:1.

Workup

  1. temperaturewith cooling at 0°-5° C
  2. customthe carbon disulfide removed
  3. additionthe residue treated with ice-water and concentrated hydrochloric acid (50 ml.)
  4. customto give 68.8 g
  5. customof 2,3-dichloro-5-phenylacetylanisole which melts at 126°-129° C. on crystallization from benzene

Sources & evidence

ORD record
ord-45beb0ed7d31489f866160cbbd7741fc
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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