Sodium Hydroxide → 4-(2-Hydroxyethanesulfonyl)-2-nitrophenol

HRID 845809Notes

Reaction equation

HRID 845809 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([S:10]([CH2:13][CH2:14][OH:15])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:16]C)([O-:3])=[O:2].[OH-].[Na+]>>[N+:1]([C:4]1[CH:9]=[C:8]([S:10]([CH2:13][CH2:14][OH:15])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:16])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 104189Ethanol, 2-[(4-methoxy-3-nitrophenyl)sulfonyl]-

Product 1

HCID 201304204-(2-Hydroxyethanesulfonyl)-2-nitrophenol

Procedure

The synthesis of 2-amino-4-(beta-sulfatoethylsulfonyl)-phenol is somewhat difficult in that it requires several reaction steps involving a high investment for equipment. In its preparation, it is necessary to start from 2-nitro-4-(beta-hydroxyethylsulfonyl)-anisole which is dealkylated by heating with aqueous sodium hydroxide solution to give 2-nitro-4-(beta-hydroxyethylsulfonyl)-phenol. The resulting phenol is then reduced to give 2-amino-4-(beta-hydroxyethyl-sulfonyl)-phenol which, in turn, must be sulfated in accordance with the disclosure of U.S. Pat. Nos. 3,364,194 or 4,334,076.

Workup

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Sources & evidence

ORD record
ord-d7481795e5ab47afb097368618c3e102
Source dataset
uspto-grants-1988_07
Patent number
US04760134

Reaction notes

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