p-Toluenesulfonic acid → 1-Acetoxy-3-methyl-1,3-butadiene

HRID 466765Notes

Reaction equation

HRID 466765 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH:4]=[O:5].[C:7](OC(C)=C)(=[O:9])[CH3:8].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:7]([O:5][CH:4]=[CH:3][C:2]([CH3:6])=[CH2:1])(=[O:9])[CH3:8]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7916Isopropenyl acetateHCID 610203-Methyl-2-butenal

Product 1

HCID 534018541-Acetoxy-3-methyl-1,3-butadiene

Procedure

Prenal (0.332 mol) was run gradually into isopropenyl acetate (0.532 mol) in which paratoluenesulphonic acid (1% by weight) had been dissolved. The acetone was distilled off as it was formed. The temperature of the mixture was 93°-94° C. at the beginning and 118° C. after heating for 1 hour 50 minutes. The 1-acetoxy-3-methylbutadiene was then purified by distillation. The boiling point of the product was 48°-52° C./13 mm Hg.

Workup

  1. dissolutionhad been dissolved
  2. distillationThe acetone was distilled off as it
  3. customwas formed
  4. customwas 93°-94° C. at the beginning and 118° C.
  5. temperatureafter heating for 1 hour 50 minutes
  6. distillationThe 1-acetoxy-3-methylbutadiene was then purified by distillation
  7. customwas 48°-52° C.

Sources & evidence

ORD record
ord-81197e3a5a2e4958854aa30f5c22fa72
Source dataset
uspto-grants-1992_10
Patent number
US05157133

Reaction notes

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