Dichloromethane → HCID 54222806, compound

HRID 1590412Notes

Reaction equation

HRID 1590412 reaction equation
[C:1]([C:6]1C=CC=CC=1P(=CCl)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[Cl:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH:31]=O.[Cl:37]CCl>>[CH2:4]([O:3][C:1](=[O:2])[C:6]([Cl:37])=[CH:31][C:30]1[CH:33]=[CH:34][C:35]([Cl:36])=[C:28]([Cl:27])[CH:29]=1)[CH3:5]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 227103,4-DichlorobenzaldehydeHCID 86746726HCID 86746726, compound

Product 1

HCID 54222806HCID 54222806, compound

Procedure

Carboethoxychloromethylenetriphenylphosphorane (8.74 g) in dichloromethane (100 ml) under nitrogen at 25° was treated with 3,4-dichlorobenzaldehyde. After 18 hours at 25° removal of solvent in vacuo was followed by trituration from hexane and the hexane washings were concentrated in vacuo. Purification by chromatrography (silica; ether/hexane) gave ethyl-3-(3,4-dichlorophenyl)-2-chloroprop-2-enoate (6.3 g).

Workup

  1. customAfter 18 hours at 25° removal of solvent in vacuo
  2. concentrationthe hexane washings were concentrated in vacuo
  3. customPurification by chromatrography (silica; ether/hexane)

Sources & evidence

ORD record
ord-0f32c4a6080a4882a2c30cf0bd19ca8c
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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