Epibromohydrin → 8-Phenyloctyloxymethyloxirane

HRID 2294331

Reaction equation

HRID 2294331 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([CH:18]1[O:20][CH2:19]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][CH2:14][O:15][CH2:16][CH:18]2[CH2:19][O:20]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 5178508-Phenyloctan-1-ol

Product 1

HCID 214747108-Phenyloctyloxymethyloxirane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 46 was repeated, except that 4 g of 8-phenyloctyl alcohol, 3.18 ml of epibromohydrin, 0.85 g of sodium hydride (as a 55% by weight dispersion in mineral oil) and 80 ml of anhydrous dimethylformamide were used, to give 2.42 g of the title compound having an Rf value of 0.51 (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-10af86dee11b4b3ea5b745844875f7d8
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Linked notes

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