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

HRID 2052022Notes

Reaction equation

HRID 2052022 reaction equation
[C:1](OC(=O)C)(=O)C.[Cl:8][C:9]1[C:14]([Cl:15])=[C:13]([C:16](=[O:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[CH:11][C:10]=1[O:25][CH3:26]>CN(CN(C)C)C>[Cl:8][C:9]1[C:14]([Cl:15])=[C:13]([C:16](=[O:24])[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH2:1])[CH:12]=[CH:11][C:10]=1[O:25][CH3:26]

Participants

4

Reactant 2

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

Product 1

HCID 109248102,3-Dichloro-4-(2-phenylacryloyl)anisole

Reagents, catalysts & solvents 1

HCID 5829N,N,N',N'-TetramethylmethanediamineSolvent

Conditions

Temperature
25 °C

Procedure

Acetic anhydride (100 ml.) is added dropwise to a suspension of 2,3-dichloro-4-phenylacetylanisole (29.5 g., 0.01 mole) in bis(dimethylamino)methane (100 ml.) under nitrogen with cooling to maintain the reaction mixture temperature below 60° C. The reaction mixture is stirred at 25° C. for 2 hours, and poured into ice water (1500 ml.) to precipitate 7.4 g. of 2,3-dichloro-4-(2-phenylacryloyl)anisole which melts at 87°-89° C.

Workup

  1. temperaturewith cooling
  2. temperatureto maintain the reaction mixture temperature below 60° C
  3. customto precipitate 7.4 g

Sources & evidence

ORD record
ord-f746fb51c32a4f03b49bdbbd403432b3
Source dataset
uspto-grants-1980_01
Patent number
US04182764

Reaction notes

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