p-Toluenesulfonic acid → 4-(2-Furyl)-2-butanone

HRID 27350

Reaction equation

HRID 27350 reaction equation
[CH3:1][C:2]([CH:4]=[CH2:5])=[O:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1>>[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:5][CH2:4][C:2](=[O:3])[CH3:1]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6570Methyl vinyl ketoneHCID 8029Furan

Product 1

HCID 127804-(2-Furyl)-2-butanoneYield 67%

Procedure

Methylvinylketone (14 g, 0.2 mol) was added dropwise over a period of about 2 hours to furan (150 ml), containing a trace of p-toluene-sulphonic acid, boiling under reflux. The dark brown reaction mixture was stirred for about 16 hours at room temperature. The excess furan was removed by distillation, after which the residue was distilled under vacuum giving 4-(2-furyl)butan-2-one (18.5 g, 67% yield). In a way analogous to that described in Example II, the ketone was reduced to the corresponding alcohol and subsequently converted to the mesylate (28 g, 92% yield).

Workup

  1. temperatureunder reflux
  2. customThe excess furan was removed by distillation
  3. distillationafter which the residue was distilled under vacuum

Sources & evidence

ORD record
ord-950327fa9df74ad2a319295d4f309b30
Source dataset
uspto-grants-1980_09
Patent number
US04221713

Linked notes

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