Dimethylformamide → 3-Chloro-3-phenyl-2-propenal

HRID 126968Notes

Reaction equation

HRID 126968 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)[CH3:12].C([O-])(=O)C.[Na+]>O>[Cl:3][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:12][CH:8]=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7410AcetophenoneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

Product 1

HCID 383893-Chloro-3-phenyl-2-propenal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

80 g Phosphoryl chloride were added dropwise to 80 ml cooled dimethyl formamide. 48 g acetophenone were added over 45 minutes and the mixture stirred at 0° C. for a further 60 minutes. After standing at room temperature overnight the mixture was poured into a solution of 600 g sodium acetate in 1500 ml water. β-Chlorocinnamaldehyde separated as a red oil. The mixture was ether extracted and the ethereal solution dried over anhydrous sodium sulphate. Evaporation of the ether yielded 44 g of β-chlorocinnamaldehyde. β-Chlorocinnamaldehyde and malonic acid were condensed to give δ-chlorocinnamylidene malonic acid and this was converted to the corresponding chlorosulphonyl derivative using the method described in Example 1(a).

Workup

  1. waitAfter standing at room temperature overnight
  2. customβ-Chlorocinnamaldehyde separated as a red oil
  3. extractionextracted
  4. dry with materialthe ethereal solution dried over anhydrous sodium sulphate
  5. customEvaporation of the ether

Sources & evidence

ORD record
ord-d1fa38287a78494593f37c85df7b2e99
Source dataset
uspto-grants-1981_03
Patent number
US04254244

Reaction notes

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