Acetic Anhydride → 2,3-Dichloro-4-(2-phenylacryloyl)anisole

HRID 1578176Notes

Reaction equation

HRID 1578176 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:4][C:3]=1[O:18][CH3:19].[C:20](OC(=O)C)(=O)C>>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:17])[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH2:20])[CH:5]=[CH:4][C:3]=1[O:18][CH3:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 111301952,3-Dichloro-4-phenylacetylanisole

Product 1

HCID 109248102,3-Dichloro-4-(2-phenylacryloyl)anisoleYield 94%

Procedure

Acetic anhydride (150 ml.) is added dropwise to a suspension of 2,3-dichloro-4-phenylacetylanisole (8.95 g., 30.3 mmol) in 15.3 ml. of N,N,N',N'-tetramethylenediaminomethane under an atmosphere of argon with ice-bath cooling. The reaction mixture stirred at 25° for 2 hrs. and poured into ice-water affords 11.9 g. of beige solid. An ethereal solution of the solid is washed with hydrochloric acid, water and then dried over magnesium sulfate. Removal of the solvent under reduced pressure provides 8.77 g. (94% yield) of 2,3-dichloro-4-(2-phenylacryloyl)anisole, m.p. 83.5°-86°.

Workup

  1. customaffords 11.9 g
  2. washAn ethereal solution of the solid is washed with hydrochloric acid, water
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of the solvent under reduced pressure
  5. customprovides 8.77 g

Sources & evidence

ORD record
ord-a5a7d2c3afef49788d78af0da3e84da3
Source dataset
uspto-grants-1981_09
Patent number
US04291168

Reaction notes

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