Water → 2-Propenoic acid, 3-phenyl-

HRID 1730875Notes

Reaction equation

HRID 1730875 reaction equation
[CH:1](=[CH:8][C:9](=[O:11])C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[O-:13].[Na+].O.[Br-].[K+]>C(Cl)(Cl)Cl>[C:9]([OH:11])(=[O:13])[CH:8]=[CH:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 159094-Phenyl-3-Buten-2-oneHCID 253877Potassium BromideHCID 23665760Sodium Hypochlorite

Product 1

HCID 87842-Propenoic acid, 3-phenyl-Yield 98.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

50 parts of benzalacetone are added slowly and in portions, in the course of 20 minutes at from 30° to 35° C, to a mixture of 900 parts by volume of sodium hypochlorite solution (containing 149 parts of sodium hypochlorite), 150 parts by volume of water and 1 part of potassium bromide. After a further reaction time of 1.5 hours at 40° C, the chloroform which has formed is separated off, the aqueous phase is acidified and the organic phase which forms is combined with the chloroform phase. The aqueous solution is extracted by shaking with a further 100 parts by volume of chloroform and the chloroform is distilled from the combined organic phases. 49.5 parts (98.5% of theory) of cinnamic acid melting at 122° C are obtained. ##SPC5##

Workup

  1. customis separated off
  2. extractionThe aqueous solution is extracted
  3. distillationthe chloroform is distilled from the combined organic phases

Sources & evidence

ORD record
ord-8c56bdfb3f944f4f879c4fa50c77771d
Source dataset
uspto-grants-1976_11
Patent number
US03994897

Reaction notes

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