Phenol → 5-Dimethylsulphamyl-3-nitro-4-phenoxy-benzoic acid

HRID 918602Notes

Reaction equation

Cl[C:2]1[C:10]([S:11](=[O:16])(=[O:15])[N:12]([CH3:14])[CH3:13])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+]>O>[CH3:13][N:12]([CH3:14])[S:11]([C:10]1[C:2]([O:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:3]([N+:17]([O-:19])=[O:18])[CH:4]=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7])(=[O:16])=[O:15]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-chloro-5-dimethylsulphamyl-3-nitro-benzoic acid (3.08 g), phenol (2 g), sodium hydrogen carbonate (3.4 g), and water (20 ml) was heated at 90°C for 8 hours. Then water (40 ml) was added and, after cooling, the 5-dimethylsulphamyl-3-nitro-4-phenoxy-benzoic acid was precipitated by acidification with 4N hydrochloric acid. After isolation by filtration and several recrystallizations from ethanol, the said compound was obtained with a melting point of 224°-226°C.

Workup

temperatureafter cooling
customthe 5-dimethylsulphamyl-3-nitro-4-phenoxy-benzoic acid was precipitated by acidification with 4N hydrochloric acid
filtrationAfter isolation by filtration and several recrystallizations from ethanol
customthe said compound was obtained with a melting point of 224°-226°C.

Sources & evidence

ORD record: ord-620fe651c61f4f868f9e86a0c92a335c
Source dataset: uspto-grants-1976_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03971819

Reaction notes

Loading…