3-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde → 3-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-methanol

HRID 615027Notes

Reaction equation

HRID 615027 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([CH:12]=[O:13])[C:9]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C.CN(C)C=O>[OH:13][CH2:12][C:10]1[C:9]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[N:8][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 7034923-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 7401783-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-methanolYield 93.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

80 grams 1-phenyl-3-(p-chlorophenyl)-pyrazol-4-aldehyde were dissolved in a mixture of 800 milliliters ethanol and 1200 milliliters dimethylformamide. To the solution thus obtained, 5.5 grams 95% sodium borohydride were added in small portions at 20°-25° C. The mixture was then stirred for one hour at room temperature. Thereafter, the reaction mixture was evaporated and the residue was taken up, with rubbing, with ethanol and water were thereafter added. The precipitate formed thereby was separated, dispersed and stirred in warm water, the precipitate was filtered off by suction, dried and recrystallized from benzene. 75 grams 4-hydroxymethyl-1-phenyl-3-(p-chlorophenyl)-pyrazol, melting at 141°-142° C., were obtained, representing a yield of 93%.

Workup

  1. customTo the solution thus obtained
  2. customThereafter, the reaction mixture was evaporated
  3. additionwere thereafter added
  4. customThe precipitate formed
  5. customthereby was separated
  6. additiondispersed
  7. stirringstirred in warm water
  8. filtrationthe precipitate was filtered off by suction
  9. customdried
  10. customrecrystallized from benzene

Sources & evidence

ORD record
ord-91a21296f2ed468281e151f75ef6dc57
Source dataset
uspto-grants-1979_03
Patent number
US04146721

Reaction notes

Loading…