2-Phenylethanol → HCID 13231993, compound

HRID 1901708Notes

Reaction equation

HRID 1901708 reaction equation
[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:12]([CH:14]1[O:16][CH2:15]1)Br>CN(C)C=O>[C:1]1([CH2:7][CH2:8][O:9][CH2:12][CH:14]2[CH2:15][O:16]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 18430EpibromohydrinHCID 24758Sodium hydride

Product 1

HCID 13231993HCID 13231993, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 46 was repeated, except that 4.28 g of 2-phenylethanol, 1.68 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 4.1 ml of epibromohydrin and 100 ml of anhydrous dimethylformamide were used. The resulting crude product was purified by silica gel column chromatography, using a 8:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 4.68 g of the title compound as a colorless oil having an Rf value of 0.77 (on silica gel thin layer chromatography, using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 46
  2. customThe resulting crude product was purified by silica gel column chromatography
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-9368b5ca647f46ea889ccff8cea29484
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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