4-Hydroxybenzaldehyde → 1,5-Bis(4-hydroxyphenyl)-1,4-pentadien-3-one

HRID 979067Notes

Reaction equation

HRID 979067 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([CH3:13])=[O:12]>C(O)C.Cl>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:9][C:2](=[O:1])[CH:3]=[CH:4][C:5]2[CH:8]=[CH:13][C:11]([OH:12])=[CH:10][CH:6]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 180Acetone

Product 1

HCID 1074411,5-Bis(4-hydroxyphenyl)-1,4-pentadien-3-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 150 g (1.23 mole) of 4-hydroxybenzaldehyde and 30 g (0.52 mole) of acetone in 600 ml of absolute ethanol was cooled while passing in hydrogen chloride for 45 minutes. After two hours of stirring, ice water was added and the resulting dark solid was filtered off. It was crystallized from absolute ethanol to give 90 g of brown, crystalline product.

Workup

  1. filtrationthe resulting dark solid was filtered off
  2. customIt was crystallized from absolute ethanol
  3. customto give 90 g of brown, crystalline product

Sources & evidence

ORD record
ord-1066eee636e441d49a322ab561fd154f
Source dataset
uspto-grants-1987_05
Patent number
US04666909

Reaction notes

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