Benzaldehyde → HCID 53986712, compound

HRID 1452309Notes

Reaction equation

HRID 1452309 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:9]([CH:10]=[CH:11][CH3:12])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](=[O:16])[CH2:14][CH3:15].C(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C(O)C.O>[OH:3][C:4]1[C:9]([CH:10]=[CH:11][CH3:12])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](=[O:16])[CH:14]=[CH:15][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54033437HCID 54033437, compound

Product 1

HCID 53986712HCID 53986712, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

60 ml of 50% (w/v) sodium hydroxide was added dropwise during 30 minutes to a solution of 17.6 g of a 7:3 E-Z mixture of 2'hydroxy-3'-(1-propenyl)propiophenone (prepared as described in R. E. Ford. et al., J. Med. Chem., 29, 538, (1986)) and 10.82 g of benzaldehyde in 73 ml of ethanol stirred at 0° C. The temperature of the reaction mixture was raised to 25° C. and stirring was continued for 4 hours. After standing at room temperature overnight, 150 ml of water was added, followed by dropwise addition of 95 ml of 37% hydrochloric acid under stirring at 0° C. The precipitated solid was filtered by suction, washed with water and desiccated, yielding 26.8 g of 1-[2-hydroxy-3-(1-propenyl)phenyl]-3-phenyl-2-propen-1-one. This material was used without further purification in the next step.

Workup

  1. temperatureThe temperature of the reaction mixture was raised to 25° C.
  2. stirringstirring
  3. waitAfter standing at room temperature overnight
  4. stirringunder stirring at 0° C
  5. filtrationThe precipitated solid was filtered by suction
  6. washwashed with water

Sources & evidence

ORD record
ord-04f9517e48364552812cda7c6e51ed3d
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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