p-Toluenesulfonic acid → HCID 20354840, compound

HRID 372120Notes

Reaction equation

HRID 372120 reaction equation
[C:1]([O:4][CH:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:6][CH2:7][CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])(=[O:3])[CH3:2].[C:19](OC(C)=C)(=[O:21])[CH3:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[C:19]([O:13][C:9]1[CH2:10][CH2:11][CH2:12][C:8]=1[CH2:7][CH2:6][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7916Isopropenyl acetateHCID 20354860HCID 20354860, compound

Product 1

HCID 20354840HCID 20354840, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(3-Acetoxyoctyl)cyclopentanone (85 g.) [prepared as described in (d) above], isopropenyl acetate (125 ml.) and p-toluenesulphonic acid (2 g.) were refluxed for 24 hours allowing the acetone formed during the reaction to slowly ditil from the head of a Dufton column. The excess isopropenyl acetate was then distilled off and the residue cooled, shaken with 2N sodium carbonate solution and extracted with diethyl ether. The combined ether extracts were dried over anhydrous magnesium sulphate and the ether removed in vacuo. Distillation of the residue gave 1-acetoxy-2-(3-acetoxyoctyl)cyclopent-1-ene (85 g.), b.p. 108°-110° C./0.03 mm.Hg; nD26 = 1.459.

Workup

  1. customformed during the reaction
  2. distillationThe excess isopropenyl acetate was then distilled off
  3. temperaturethe residue cooled
  4. extractionextracted with diethyl ether
  5. dry with materialThe combined ether extracts were dried over anhydrous magnesium sulphate
  6. customthe ether removed in vacuo
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-cc34440732ac4e02b56b5b336072f99c
Source dataset
uspto-grants-1978_05
Patent number
US04088821

Reaction notes

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