4-Hydroxybenzaldehyde → 3-Phenylpropanamide

HRID 634786Notes

Reaction equation

HRID 634786 reaction equation
OCC([NH:6][C:7](=[O:16])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)CO.OC1C=CC(C=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:10]1([CH2:9][CH2:8][C:7]([NH2:6])=[O:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 21260455N-(2-hydroxy-1-hydroxymethyl-ethyl)-3-phenyl-propionamide

Product 1

HCID 76253-PhenylpropanamideYield 124.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-(2-hydroxy-1-hydroxymethyl-ethyl)-3-phenyl-propionamide (1.7 g, 7.6 mmol), toluene (70 ml), 4-hydroxybenzaldehyde (1.856 g, 15.2 mmol) and a catalytic amount of p-toluenesulfonic acid was refluxed for 3 h. The mixture was evaporated and CH2Cl2 was added to the residue. The precipitate was filtered off and recrystallised from hot AcOEt (50 ml). The light brown crystals formed collected yielding trans-N-12-(4-hydroxy-phenyl)-[1,3]dioxan-5-yl]-3-phenyl-propionamide (1.41 g, MS: m/e=328.2 (M+H+)). The filtrate was concentrated and left at 4° overnight. The newly formed crystals are collected yielding cis-N-[2-(4-hydroxy-phenyl)-[1,3]dioxan-5-yl]-3-phenyl-propionamide (0.401 g, m/e=326.4 (M−H+)).

Workup

  1. customThe mixture was evaporated
  2. additionCH2Cl2 was added to the residue
  3. filtrationThe precipitate was filtered off
  4. customrecrystallised from hot AcOEt (50 ml)
  5. customThe light brown crystals formed
  6. customcollected

Sources & evidence

ORD record
ord-fc50e73a665b45e0a16912710a43f4a3
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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