4-Hydroxybenzaldehyde → HCID 2831271, compound

HRID 1721508Notes

Reaction equation

HRID 1721508 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1>C(O)C>[OH:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[N:9][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 2831271HCID 2831271, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.96 g (0.082 mole) of (R)-(+)-1-phenylethylamine and 10.54 g (0.086 mole) of p-hydroxybenzaldehyde were dissolved in 140 ml of ethyl alcohol, and the resulting solution was stirred under reflux for 2 hours. The reaction mixture was cooled to room temperature, and the crystalline material thus formed was separated by filtration to give 13.0 g of (-)-N-(p-hydroxybenzylidene)-1-phenylethylamine. Yield: 70.4%. m.p. 176°-178° C.; α!D22 -120.7° (C 1.0, MeOH) NMR-spectral data (δ ppm, DMSO-d6) 1.50 (d) 3H; 4.50 (q) 1H; 6.7-7.8 (m) 9H; 7-7.8 (broad) 1H; 8.34 (s) 1H

Workup

  1. temperatureunder reflux for 2 hours
  2. customthe crystalline material thus formed
  3. customwas separated by filtration

Sources & evidence

ORD record
ord-d2c0db0b54774cf8833bed85bb1ddc73
Source dataset
uspto-grants-1996_04
Patent number
US05510519

Reaction notes

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