Acetophenone → 18365-42-9

HRID 444300Notes

Reaction equation

HRID 444300 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[CH3:7].[C:15]([O-:18])(=O)C.[Na+]>CN(C)C=O.O>[Cl:3][C:7](=[CH:6][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:15]=[O:18]

Participants

6

Reactant 3

HCID 7410AcetophenoneHCID 24813Phosphorus oxychloride2×HCID 517045Sodium Acetate

Product 1

HCID 2904218365-42-9

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

β chlorocinnamaldehyde was prepared by the following method. Phosphoryl chloride (24 ml, 0.26 mol.) was slowly added to anhydrous dimethyl formamide (40 ml) maintaining a temperature of 0° C. and the resulting solution stirred for 30 minutes. Acetophenone (24 g 0.2 mol.) was also dissolved in anhydrous dimethyl formamide (25 ml) and the mixture slowly added to the phosphoryl chloride solution. Whilst stirring, the reaction mixture was allowed to attain room temperature, stirred for two hours and then poured into an agitated solution of sodium acetate (300 g) in water (750 ml), After stirring for 30 minutes the product was extracted into ether, the ether extracts were dried over magnesium sulphate and the ether was then removed to yield 28.8 g of crude product which was used without further purification as follows.

Workup

  1. stirringWhilst stirring
  2. customto attain room temperature
  3. stirringstirred for two hours
  4. stirringAfter stirring for 30 minutes the product
  5. extractionwas extracted into ether
  6. dry with materialthe ether extracts were dried over magnesium sulphate
  7. customthe ether was then removed

Sources & evidence

ORD record
ord-34e0e119e042404f9d996d760c9d86d1
Source dataset
uspto-grants-1981_04
Patent number
US04263394

Reaction notes

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