Vinyloxirane → 2-Buten-1-ol

HRID 1654281Notes

Reaction equation

HRID 1654281 reaction equation
[O:1]1[CH2:5][CH:2]1[CH:3]=[CH2:4].[O:6]1[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14])[CH2:7]1.[H][H].[S]>[Ni]>[O:1]1[CH2:5][CH:2]1[CH:3]=[CH2:4].[CH2:7]([OH:6])[CH:8]=[CH:9][CH3:10].[CH2:5]([OH:1])[CH2:2][CH:3]=[CH2:4].[O:6]1[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14])[CH2:7]1

Participants

9

Reactant 4

HCID 13586VinyloxiraneHCID 296782-(Hex-5-en-1-yl)oxiraneHCID 5362487SulfurHCID 178418361HCID 178418361, compound

Product 4

HCID 13586VinyloxiraneHCID 200242-Buten-1-olYield 74%HCID 296782-(Hex-5-en-1-yl)oxiraneHCID 693893-Buten-1-olYield 23%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

The significance of the conjugated epoxyalkene system in the reactants of this invention is demonstrated by the hydrogenation of 3,4-epoxy-1-butene and 1,2-epoxy-7-octene under mild conditions of 50°-55° C. and 4.6 bars hydrogen pressure using a sulfur-modified Raney-nickel catalyst. Such hydrogenation of 3,4-epoxy-1-butene gives 74% crotyl alcohol and 23% 3-buten-1-ol whereas the hydrogenation of 1,2-epoxy-7-octene (wherein the double bond and epoxy groups are separated by four carbon atoms) gives a mixture of starting material, 1,2-epoxyoctane, and isomers of the starting material.

Sources & evidence

ORD record
ord-90bb9d1142a34d129d1e455dcae6ab69
Source dataset
uspto-grants-1995_04
Patent number
US05406007

Reaction notes

Loading…