Dimethylformamide → 4-Chloro-2-[chloro(4-methylphenyl)methylidene]butanal

HRID 274248Notes

Reaction equation

HRID 274248 reaction equation
O=P(Cl)(Cl)[Cl:3].[Cl:6][CH2:7][CH2:8][C:9](=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.CN([CH:22]=[O:23])C>>[Cl:3][C:10]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)=[C:9]([CH2:8][CH2:7][Cl:6])[CH:22]=[O:23]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 57318013HCID 57318013, compound

Product 1

HCID 540572204-Chloro-2-[chloro(4-methylphenyl)methylidene]butanal

Conditions

Temperature
50 °C

Procedure

390 ml of POCl3 are introduced dropwise, at a temperature of between 7° and 12° C., into a solution of 352.5 g of 4-chloro-1-(4-methylphenyl)butanone, prepared above according to Example 12 a), in 450 ml of DMF. The temperature is raised gradually, in the first instance to 50° C. over 2 h and then to 75° C. over 45 min. The mixture is poured on to ice and extracted three times with ether and the organic phases are combined, washed with water and then dried and evaporated to give 387.8 g of 3-chloro-2-(2-chloroethyl)-3-(4-methylphenyl)prop-2-en-1-al in the form of an oil, which is used as such in the next step.

Workup

  1. customprepared
  2. additionThe mixture is poured on to ice
  3. extractionextracted three times with ether
  4. washwashed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-7bad4485665b476d97accd94181b8d3d
Source dataset
uspto-grants-1995_02
Patent number
US05389632

Reaction notes

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