3-Phenylprop-2-Enal → 4-Chloro-3,3-dimethyl-6-phenylhex-5-en-2-one

HRID 981796Notes

Reaction equation

HRID 981796 reaction equation
[CH:1](=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:11]([C:14]([CH3:16])=[O:15])([CH3:13])[CH3:12].[ClH:17].C(=O)([O-])[O-].[Na+].[Na+]>>[C:4]1([CH:3]=[CH:2][CH:1]([Cl:17])[C:11]([CH3:13])([CH3:12])[C:14](=[O:15])[CH3:16])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 3073-Phenylprop-2-EnalHCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 112513-Methyl-2-butanone

Product 1

HCID 541173564-Chloro-3,3-dimethyl-6-phenylhex-5-en-2-one

Procedure

20 g (0.15 mol) of cinnamaldehyde and 25.8 g (0.3 mol) of methyl isopropyl ketone are initially introduced, and dry hydrogen chloride is passed in at 10° C. until saturation. The mixture is stirred for 12 hours at 20°-25° C. and poured onto water, and the resulting mixture is neutralized by means of sodium carbonate. The neutralized mixture is extracted with methylene chloride and dried, and the methylene chloride is distilled off. 25.7 g (72.4% of theory) are obtained of 1-phenyl-3-chloro-4,4-dimethyl-1-hexen-5-one which has a melting point of 71° C.

Workup

  1. customis passed in at 10° C. until saturation
  2. additionpoured onto water
  3. extractionThe neutralized mixture is extracted with methylene chloride
  4. customdried
  5. distillationthe methylene chloride is distilled off

Sources & evidence

ORD record
ord-4560a2f37cc8474885424e9f5afa7a65
Source dataset
uspto-grants-1991_02
Patent number
US04992577

Reaction notes

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