2-Aminophenol → p-Toluenesulfonic acid

HRID 258554Notes

Reaction equation

HRID 258554 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9]([N:16]1[CH2:21][CH2:20][O:19][CH:18]([CH2:22][O:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([N:16]1[CH2:21][CH2:20][O:19][CH:18]([CH2:22][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])[CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1.[C:30]1([CH3:33])[CH:29]=[CH:28][C:27]([S:24]([OH:26])(=[O:23])=[O:25])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 58012-AminophenolHCID 122977674-Benzyl-2-toluene-p-sulphonyloxymethylmorpholine

Product 2

HCID 6101p-Toluenesulfonic acidHCID 203639264-Benzyl-2-(2-hydroxyanilinomethyl)morpholine

Conditions

Temperature
200 °C

Procedure

A mixture of o-aminophenol (15 g.) and 4-benzyl-2-(toluene-p-sulphonyloxymethyl)morpholine (30 g.) was heated at 200° C. for 1 hour in an atmosphere of nitrogen. The reaction product was crystallised from ethanol to give 4-benzyl-2-(2-hydroxyanilinomethyl)morpholine as the toluene-p-sulphonic acid salt, m.p. 188°-190° C., which was hydrogenated in ethanol at atmospheric pressure using a 10% palladium-on-carbon catalyst. There was thus obtained 2-(2-hydroxyanilinomethyl)morpholine as the toluene-p-sulphonic acid salt, m.p. 176°-178° C. on recrystallisation from ethanol.

Workup

  1. customThe reaction product was crystallised from ethanol

Sources & evidence

ORD record
ord-4e73915b193441b8b2ed1e39f654d967
Source dataset
uspto-grants-1977_07
Patent number
US04033951

Reaction notes

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