Water → HCID 54204550, compound

HRID 363990Notes

Reaction equation

HRID 363990 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]=[CH:17][C:18](=[O:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].O>C(C(C)=O)C>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]=[CH:17][C:18](=[O:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 979566051-53-2

Product 1

HCID 54204550HCID 54204550, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of benzylchloride (8.8 g), 4-(2-hydroxy phenyl)-but-3-en-2-one (11.4 g) and anhydrous potassium carbonate (11.0 g) in methyl ethyl ketone (100 ml) was stirred and heated under reflux for 5 hours. The mixture was poured into water (300 ml) and extracted with chloroform (200 ml). The chloroform extracts were washed with dilute sodium hydroxide solution and then dried over magnesium sulphate and evaporated to give 4-(2-benzyloxyphenyl)-but-3-en-2-one (15 g) as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. extractionextracted with chloroform (200 ml)
  4. washThe chloroform extracts were washed with dilute sodium hydroxide solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-2187e50b08244c0499857fb2ed4c55f2
Source dataset
uspto-grants-1986_08
Patent number
US04604128

Reaction notes

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