Benzaldehyde → 3-(4-Hydroxyphenyl)-1-phenylprop-2-en-1-one

HRID 24958Notes

Reaction equation

HRID 24958 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=O.[OH-].[Na+].[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([CH:2]=[CH:1][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:20])=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 74694'-HydroxyacetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 893403-(4-Hydroxyphenyl)-1-phenylprop-2-en-1-oneYield 50%

Procedure

The photo-reactive group of the side chain was synthesized as follows. First, 10.2 g (0.075 mol) of 4-hydroxyacetophenone was dissolved into 0.7 w/v % aqueous solution of NaOH. Benzaldehyde (8 g (0.075 mol)) then was added and the resulting solution was stirred for 8 hours at a room temperature. Then, the solution was neutralized with 5N HCl to yield 4-hydroxychalcone at 50% yield as follows.

Workup

  1. customThe photo-reactive group of the side chain was synthesized

Sources & evidence

ORD record
ord-4ebde6e3e5484ef4a7fc46cc20cef663
Source dataset
uspto-grants-2005_02
Patent number
US06858269B2

Reaction notes

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