Water → HCID 54512219, compound

HRID 1612620Notes

Reaction equation

HRID 1612620 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:21])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].O>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:21])[CH:10]=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([N:18]([CH3:19])[CH3:20])=[CH:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 284107HCID 284107, compoundHCID 4311764Sodium borohydride2×

Product 1

HCID 54512219HCID 54512219, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4-methoxyphenyl)-3-(4-dimethylaminophenyl)-1-oxo-prop-2-ene (14.1 g, 0.05 mol) was dispersed in methanol (100 ml). Sodium borohydride (5.6 g, 0.15 mol) was added slowly at ambient temperature under vigorous stirring. After completion of the addition of sodium borohydride the reaction mixture was kept stirred at ambient temperature for 5 hours. When the reaction was complete, the reaction mixture was poured into water (500 ml), and extracted with toluene. The toluene was removed using a rotary evaporator leaving an oily residue. The crude product was crystallized from methanol to give 1-(4-methoxyphenyl)-3-(4-dimethylaminophenyl)prop-2-en-1-ol as a white coloured solid in a yield of 4.0 g (28.3% of theory) with a melting point of 137-148° C.

Workup

  1. extractionextracted with toluene
  2. customThe toluene was removed
  3. customa rotary evaporator
  4. customleaving an oily residue
  5. customThe crude product was crystallized from methanol

Sources & evidence

ORD record
ord-c4e8b66808bf463d91b3c3dab100871e
Source dataset
uspto-grants-1993_03
Patent number
US05190909

Reaction notes

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