3',5'-Dichloro-2'-hydroxyacetophenone → 2,4-Dichloro-6-(1'-hydroxyethyl)phenol

HRID 894228Notes

Reaction equation

HRID 894228 reaction equation
[CH3:1][C:2]([C:4]1[C:9]([OH:10])=[C:8]([Cl:11])[CH:7]=[C:6]([Cl:12])[CH:5]=1)=[O:3].[BH4-].[Na+]>C(O)C>[Cl:11][C:8]1[CH:7]=[C:6]([Cl:12])[CH:5]=[C:4]([CH:2]([OH:3])[CH3:1])[C:9]=1[OH:10]

Participants

4

Reactant 2

HCID 5206083',5'-Dichloro-2'-hydroxyacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 211628312,4-Dichloro-6-(1'-hydroxyethyl)phenolYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-Dichloro-2-hydroxyacetophenone (40 g) was treated in ethanol with sodium borohydride (4 g). The solid reaction product was recrystallized from benzene to give 2,4-dichloro-6-(1'-hydroxy ethyl) phenol (32 g, m.p. 70°).

Workup

  1. customThe solid reaction product
  2. customwas recrystallized from benzene

Sources & evidence

ORD record
ord-09bbc22672b540f3bb76d10ec4c56923
Source dataset
uspto-grants-1981_08
Patent number
US04282390

Reaction notes

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