Benzaldehyde → 2-Propen-1-one, 1-[2-hydroxy-4-(phenylmethoxy)phenyl]-3-phenyl-

HRID 1719514Notes

Reaction equation

HRID 1719514 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[OH:18])=[O:3].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>C(O)C>[O:3]=[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[OH:18])[CH:1]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 3092574'-Benzyloxy-2'-hydroxyacetophenone

Product 1

HCID 27779242-Propen-1-one, 1-[2-hydroxy-4-(phenylmethoxy)phenyl]-3-phenyl-Yield 166.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17.63 g (72.6 mmoles) of 2-hydroxy-4-benzyloxyacetophenone, 17.60 g (165.8 mmoles) of benzaldehyde and 35.20 g of 50% strength sodium hydroxide solution in 200 ml of ethanol were stirred for 3 days, during which crystals precipitated. The crystal sludge was acidified with 100 ml of 5N hydrochloric acid and was stirred for 10 minutes. The mixture was filtered with suction to give 40.0 g of moist crystals. The crude product was recrystallized from 800 ml of ethanol.

Workup

  1. customprecipitated
  2. filtrationThe mixture was filtered with suction

Sources & evidence

ORD record
ord-91213319c507422e9223f9dc1f712460
Source dataset
uspto-grants-1985_09
Patent number
US04540697

Reaction notes

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