Catechol → (1,1'-Biphenyl)-2,3'-diol

HRID 905115Notes

Reaction equation

HRID 905115 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)O)[OH:2].[OH-:9].[Na+]>O>[CH:1]1[CH:3]=[C:5]([C:7]2[CH:6]=[CH:5][CH:3]=[C:1]([OH:2])[CH:8]=2)[C:6]([OH:9])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 289Catechol2×HCID 14798Sodium Hydroxide

Product 1

HCID 33665(1,1'-Biphenyl)-2,3'-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In this two step synthesis, the first step is the reaction of bis-2-chloroethyl ether with catechol and sodium hydroxide in water. An excess of catechol and a controlled amount of base are used to produce the diphenol (j) without employing a blocking group. The diphenol (j) precipitates from the reaction solution and is washed with water to remove contaminating catechol. The diphenol (j) is then recrystallized from methanol. Based upon the limiting reagent bis-2-chloroethyl ether (i) 40% yields (200 gs) of diphenol (j) have been obtained.

Workup

  1. customIn this two step synthesis

Sources & evidence

ORD record
ord-6b82062265114a659ef9a7e0bb3b191d
Source dataset
uspto-grants-1983_12
Patent number
US04421923

Reaction notes

Loading…