p-Toluenesulfonic acid → 2-Methyl-4,4-bis[(3-methylbut-2-en-1-yl)oxy]but-1-ene

HRID 1707133Notes

Reaction equation

HRID 1707133 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH:4]=[O:5].[C:7]1([CH3:17])[CH:12]=[CH:11]C(S(O)(=O)=O)=C[CH:8]=1>C1C=CC=CC=1>[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][O:5][CH:4]([O:5][CH2:11][CH:12]=[C:7]([CH3:8])[CH3:17])[CH2:3][C:2]([CH3:6])=[CH2:1]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 610203-Methyl-2-butenal

Product 1

HCID 215894552-Methyl-4,4-bis[(3-methylbut-2-en-1-yl)oxy]but-1-ene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2.67 parts of 3-methylbutenal, 5.5 parts of pulenol, 0.001 part of p-toluenesulfonic acid, and 20 vol. parts of benzene were charged to the same rectification column employed in Example 53, and reacted at 90° C. for 2 hours, while the volume of the system was maintained constant by feeding 10 vol. parts of fresh benzene per hour and distilling 10 vol. parts per hour of the water-containing benzene off from the system. Thus 100% of 3-methyl-3-butenal-1 was converted and 3-methyl-3-butenal-1-dipulenylacetal was obtained with the selectivity of 80.2%.

Workup

  1. customreacted at 90° C. for 2 hours, while the volume of the system
  2. temperaturewas maintained constant
  3. distillationdistilling 10 vol. parts per hour of the water-
  4. additioncontaining benzene off from the system

Sources & evidence

ORD record
ord-ac6e323ae75249f39151a7a6a17a1954
Source dataset
uspto-grants-1980_06
Patent number
US04209644

Reaction notes

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