4-Hydroxybenzaldehyde → 1-(4-Hydroxyphenyl)-5-phenylpenta-1,4-dien-3-one

HRID 615651Notes

Reaction equation

HRID 615651 reaction equation
[C:1]1([CH:7]=[CH:8][C:9](=[O:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[OH-].[Na+].Cl>C(O)C.O>[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH:10][C:9](=[O:11])[CH:8]=[CH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 159094-Phenyl-3-Buten-2-one

Product 1

HCID 541601711-(4-Hydroxyphenyl)-5-phenylpenta-1,4-dien-3-oneYield 30.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-Phenylbut-1-en-3-one (58.4 g), and p-hydroxybenzaldehyde (48.8 g) are dissolved in ethanol (300 ml) and cooled to a temperature below 15° C., using an ice bath. A solution of sodium hydroxide (20 g) in water (80 ml) is added over 2 hours, the temperature of the mixture being kept below 15° C. This solution is then neutralised to pH 7 with dilute hydrochloric acid. An oily solid separates out, and this is filtered and washed with toluene to give 30.5 g of 1-(p-hydroxyphenyl)-5-phenylpenta-1,4-dien-3-one.

Workup

  1. temperaturecooled to a temperature below 15° C.
  2. custombeing kept below 15° C
  3. filtrationAn oily solid separates out, and this is filtered
  4. washwashed with toluene

Sources & evidence

ORD record
ord-262df58532c346d089ae923f1e136a97
Source dataset
uspto-grants-1985_02
Patent number
US04500629

Reaction notes

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