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

HRID 1583559Notes

Reaction equation

HRID 1583559 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-63f5e7125bb54576beb9264b163a5de6
Source dataset
uspto-grants-1985_11
Patent number
US04552876

Reaction notes

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