p-Toluenesulfonic acid → 1-(3,5-Dichloro-2-hydroxyphenyl)-1-(5-fluoro-2-hydroxy phenyl) ethane

HRID 894229Notes

Reaction equation

HRID 894229 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH:9](O)[CH3:10])[C:3]=1[OH:12].[F:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:9]([C:18]2[CH:19]=[C:14]([F:13])[CH:15]=[CH:16][C:17]=2[OH:20])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 97324-FluorophenolHCID 211628312,4-Dichloro-6-(1'-hydroxyethyl)phenol

Product 1

HCID 570669341-(3,5-Dichloro-2-hydroxyphenyl)-1-(5-fluoro-2-hydroxy phenyl) ethane

Procedure

2,4-Dichloro-6-(1'-hydroxyethyl)phenol (10 g) was added in small portions to a melt of 4-fluoro phenol containing a trace of p-toluenesulphonic acid at 90° over a half hour period. The reaction mixture was stirred for a further 1/2 hr and cooled. The crystallization from benzene gave 1-(3,5-dichloro-2-hydroxyphenyl)-1-(5-fluoro-2-hydroxy phenyl) ethane (11 g, m.p. 150°).

Workup

  1. temperaturecooled
  2. customThe crystallization from benzene

Sources & evidence

ORD record
ord-3ff451fe676c4446a1ef768612a879b5
Source dataset
uspto-grants-1981_08
Patent number
US04282390

Reaction notes

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