Benzamide, 2-(hydroxyphenylmethyl)-N-methyl- → 3-Phenylphthalide

HRID 46809

Reaction equation

HRID 46809 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[C:4]([C:9](NC)=[O:10])=[CH:5][CH:6]=[CH:7][CH:8]=1>ClC1C=CC=CC=1Cl>[C:13]1([CH:2]2[C:3]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:9](=[O:10])[O:1]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 12241019Benzamide, 2-(hydroxyphenylmethyl)-N-methyl-

Product 1

HCID 953653-Phenylphthalide

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 76.5 g. of α-hydroxy-N-methyl-α-phenyl-o-toluamide and (0.314 mole) 150 ml. o-dichlorobenzene is heated at reflux for 18 hours. The mixture is cooled and filtered and the resulting solid triturated with cold ether to give 3-phenyl phthalide.

Workup

  1. additionA mixture of 76.5 g
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. customthe resulting solid triturated with cold ether

Sources & evidence

ORD record
ord-4b3c7438c38d418da5e52322298dbec5
Source dataset
uspto-grants-1979_11
Patent number
US04175191

Linked notes

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