Water → 2,2'-[(2-Hydroxy-5-nitro-1,3-phenylene)bis(methylene)]bis(4-chlorophenol)

HRID 894225Notes

Reaction equation

HRID 894225 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([CH2:12]Cl)[C:4]=1[OH:14].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.[OH2:23]>[N+](C1C=CC=CC=1)([O-])=O.[Cl-].[Cl-].[Zn+2]>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH:17]=1)[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([CH2:12][C:20]2[CH:21]=[C:16]([Cl:15])[CH:17]=[CH:18][C:19]=2[OH:23])[C:4]=1[OH:14]

Participants

6

Reactant 3

HCID 962WaterHCID 46844-ChlorophenolHCID 5268855HCID 5268855, compound

Product 1

HCID 130642342,2'-[(2-Hydroxy-5-nitro-1,3-phenylene)bis(methylene)]bis(4-chlorophenol)

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7416NitrobenzeneSolvent

Procedure

The 2,6-bis(chloromethyl)-4-nitrophenol (8 g) and p-chlorophenol (8.7 g) were dissolved in nitrobenzene (125 ml) at 25°. After cooling to 10° ZnCl2 (28 g) was added over 1 hr. The stirred mixture was held at room temperature for 30 hrs and poured into 200 mls of water. The organic layer was washed with water and the nitrobenzene removed by vacuum distillation. Column chromatography gave 1.5 g of 2,6-bis(5-chloro-2-hydroxybenzyl)-4-nitrophenol (mp 220°).

Workup

  1. additionwas added over 1 hr
  2. washThe organic layer was washed with water
  3. customthe nitrobenzene removed by vacuum distillation

Sources & evidence

ORD record
ord-5330c68da43f4564afbd0fd18f19252d
Source dataset
uspto-grants-1981_08
Patent number
US04282390

Reaction notes

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