Dimethyl Sulfoxide → {[(Prop-1-en-1-yl)oxy]methyl}benzene

HRID 1840699Notes

Reaction equation

HRID 1840699 reaction equation
[CH3:1]S(C)=O.[CH3:5][C:6](C)([O-])[CH3:7].[K+].[OH2:11].[CH3:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[CH:5]([O:11][CH2:1][C:14]1[CH:13]=[CH:12][CH:17]=[CH:16][CH:15]=1)=[CH:6][CH3:7]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8058HexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 54218220{[(Prop-1-en-1-yl)oxy]methyl}benzeneYield 870.4%

Conditions

Temperature
100 °C

Procedure

A mixture of 299 g of the crude product, 300 g of dimethyl sulfoxide, and 22.5 g (0.2 mol) of potassium t-butoxide was heated at 100° C. on the oil bath and ripened for 2 hours at the temperature. The solution was allowed to cool, and 650 g of water and 600 g of n-hexane were added thereto, from which the organic layer was collected. The organic layer was washed with 250 g of water, and the solvent was distilled off in vacuum, leaving 300 g of an oily substance. The oily substance was subjected to vacuum distillation, obtaining 258 g of the end product, benzyl propenyl ether. The yield was 87% (two steps) and the purity was 99.4% as analyzed by gas chromatography.

Workup

  1. temperatureto cool
  2. customfrom which the organic layer was collected
  3. washThe organic layer was washed with 250 g of water
  4. distillationthe solvent was distilled off in vacuum
  5. customleaving 300 g of an oily substance
  6. distillationThe oily substance was subjected to vacuum distillation

Sources & evidence

ORD record
ord-cd9a0cd955e741fc8d3c29fa9ffd6a94
Source dataset
uspto-grants-2004_01
Patent number
US06682869B2

Reaction notes

Loading…