4-Methylcatechol → 4-(4-Chloro-3-nitrophenylsulphonyl)-5-methyl-1,2-benzenediol

HRID 745797Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][C:15]1[CH:16]=[C:17]([OH:22])[C:18]([OH:21])=[CH:19][CH:20]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:20]2[CH:19]=[C:18]([OH:21])[C:17]([OH:22])=[CH:16][C:15]=2[CH3:14])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

Reactant 2

HCID 99584-Methylcatechol

HCID 40975444-Chloro-3-nitrobenzenesulfinic acid

Product 1

HCID 233120834-(4-Chloro-3-nitrophenylsulphonyl)-5-methyl-1,2-benzenediol

Procedure

66 g (297.8 mmol) of 4-chloro-3-nitrobenzenesulphinic acid (produced by reduction of 4-chloro-3-nitrobenzenesulphonyl chloride with sodium sulphite) are condensed with 41.95 g (337.9 mmol) of 4-methyl-1,2-benzenediol in a manner analogous to that described in Example 4, yielding 4-(4-chloro-3-nitrophenylsulphonyl)-5-methyl-1,2-benzenediol in the form of crystals having a melting point of 196°-197° (from ethyl acetate/hexane).

Sources & evidence

ORD record: ord-84065377be804fb49823923b6813b87c
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04600709

Reaction notes

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