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

HRID 1156197Notes

Reaction equation

HRID 1156197 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 icebath 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-07edd047e7f9456287c19ee4838d8d9b
Source dataset
uspto-grants-1982_06
Patent number
US04334088

Reaction notes

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