Epibromohydrin → 7-Phenylheptyloxymethyloxirane

HRID 2294334Notes

Reaction equation

HRID 2294334 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([CH:17]1[O:19][CH2:18]1)Br.[H-].[Na+]>CN(C)C=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:17]2[CH2:18][O:19]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 154271Benzeneheptanol

Product 1

HCID 214747647-Phenylheptyloxymethyloxirane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 46 was repeated, except that 2 g of 7-phenylheptyl alcohol, 1.7 ml of epibromohydrin, 0.44 g of sodium hydride (as a 55% by weight dispersion in mineral oil) and 50 ml of anhydrous dimethylformamide were used, to give 1.15 g of the title compound having an Rf value of 0.49 (on silica gel thin layer chromatography, using a 1:6 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 46

Sources & evidence

ORD record
ord-50711051149043619a8df4a049e26e6d
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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