4-Hydroxybiphenyl → 1-(Biphenyl-4-yloxy)-2,3-epoxypropane

HRID 2294345Notes

Reaction equation

HRID 2294345 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([CH:16]1[O:18][CH2:17]1)Br.[H-].[Na+]>CN(C)C=O>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH:16]3[CH2:17][O:18]3)=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 18430EpibromohydrinHCID 24758Sodium hydride

Product 1

HCID 1073251-(Biphenyl-4-yloxy)-2,3-epoxypropaneYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in preparation 46 was repeated, except that 4.00 g of 4-phenylphenol, 3.97 g of epibromohydrin, 1.27 g of sodium hydride (as a 55% by weight dispersion in mineral oil) and 80 ml of anhydrous dimethylformamide were used, to give 4.43 g of the title compound, melting at 80.2° to 82.9° C.

Workup

  1. customA procedure similar to that described in preparation 46

Sources & evidence

ORD record
ord-c26d4d6a4ee44fed8fc7e152857be830
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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