p-Toluenesulfonic acid → Dimethylallyl ether

HRID 1764765Notes

Reaction equation

HRID 1764765 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][OH:5].[C:7]1([CH3:17])[CH:12]=CC(S(O)(=O)=O)=[CH:9][CH:8]=1>>[CH2:4]([O:5][CH2:9][CH:8]=[C:7]([CH3:17])[CH3:12])[CH:3]=[C:2]([CH3:6])[CH3:1]

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 111733-Methyl-2-buten-1-OL

Product 1

HCID 10920736Dimethylallyl etherYield 50%

Procedure

To 30 g of 3-methyl-2-buten-1-ol [prenol] was added 0.74g of p-toluenesulfonic acid, and the mixture was stirred under reflux (at 130°-140° C.) for 3 hours. The reaction solution separated into two layers. The lower layer comprised water and the upper layer was subjected to gas chromatographic analysis revealing that about 4% of the starting prenol remained and that diprenyl ether was formed in a yield of about 50% based on the starting prenol together with unknown products. After distillation under reduced pressure was isolated diprenyl ether having the following properties.

Workup

  1. temperatureunder reflux (at 130°-140° C.) for 3 hours
  2. customThe reaction solution separated into two layers

Sources & evidence

ORD record
ord-984d781dcbaa4c69b139a8f80a19553b
Source dataset
uspto-grants-1978_09
Patent number
US04117247

Reaction notes

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