4-Hydroxybenzaldehyde → HCID 22168763, compound

HRID 1510966Notes

Reaction equation

HRID 1510966 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.[CH3:16][C:17]1[N:21]([CH:22](S(OC)(=O)=O)[CH3:23])[C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:19][CH:18]=1>CN(C)C=O.O>[CH3:16][C:17]1[N:21]([CH2:22][CH2:23][O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 22168755HCID 22168755, compound

Product 1

HCID 22168763HCID 22168763, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of potassium carbonate (16.43 g) in dimethyl formamide (50 mL), 4-hydroxy benzaldehyde (4.37 g) was added and warmed to 90-C to 95° C. To the solution, methyl 1-[5-methyl-2-phenyl-1H-pyrrol-1yl]ethane sulfonate (10 g) (compound no. 64 dissolved in dimethyl formamide (50 mL) w added within 30 min and the reaction was continued for further 4 hours. The reaction mixture was diluted with water (100 mL) and was extracted with ethyl acetate (3×100 mL), washed with water (3×100 mL), brine (200 mL), and was dried over sodium sulfate. The solvent was evaporated under reduced pressure, to yield the title compound.

Workup

  1. additionwas added
  2. additionadded within 30 min
  3. extractionwas extracted with ethyl acetate (3×100 mL)
  4. washwashed with water (3×100 mL), brine (200 mL)
  5. dry with materialwas dried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-70efd0f4b6f34b3e8c95bff596ff416c
Source dataset
uspto-grants-2012_07
Patent number
US08212057B2

Reaction notes

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