2,4,5-Trichlorophenol → 2-Chloro-4-nitro-3-phenoxy-1-(2,4,5-trichloro-phenoxy)benzene

HRID 1902588Notes

Reaction equation

[Cl:1][C:2]1[C:7](Cl)=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[CH:22][C:21]=1[OH:28].[OH-].[Na+]>CS(C)=O>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[O:28][C:21]1[CH:22]=[C:23]([Cl:27])[C:24]([Cl:26])=[CH:25][C:20]=1[Cl:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 28.4 gm of 2,3-dichloro-6-nitro-1-phenoxy-benzene, 21.6 gm of 2,4,5-trichloro-phenol, 10 ml of 10 N sodium hydroxide and 80 ml of dimethylsulfoxide was stirred for 6 hours at 100° C. Thereafter, the reaction mixture was admixed with 600 ml of 1 N sodium hydroxide, and the precipitated product was collected by suction filtration and recrystallized from 150 ml of ethanol. 31 gm (77.4% of theory) of the title compound, m.p. 112° C., were obtained. An additional amount of the product (about 6 gm) was obtained by evaporating the filtrate.

Workup

filtrationthe precipitated product was collected by suction filtration
customrecrystallized from 150 ml of ethanol

Sources & evidence

ORD record: ord-4205c1fc485e4028b651136ca2067ab3
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04364875

Reaction notes

Loading…