p-Toluenesulfonic acid → HCID 642972, compound

HRID 716499Notes

Reaction equation

HRID 716499 reaction equation
[CH3:1][C:2]1[CH:3]=CC(S(O)(=O)=O)=[CH:6][CH:7]=1.[C:12]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13]1.CC(CCO)=C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH2:3][C:12]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[O:17][CH2:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8452CyclopentanoneHCID 129883-Methyl-3-buten-1-ol

Product 1

HCID 642972HCID 642972, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of p-TSA (20 g, 0.105 mol) and toluene (2 L) was heated to 115° C. To this mixture were added cyclopentanone (840 g, 10 mols) and isoprenol (946 g, 11 mols) and heated further for 3-6 h. Water was removed from the reaction azeotropically. The reaction mixture was then cooled to room temperature. The organic phase was washed with a 5% Na2CO3 solution, washed with water dried and concentrated and distilled further to provideto 9-methyl-6-oxaspiro[4.5]dec-8-ene (0.851 kg) having a purity of 95% (sum of the isomers) for a total yield of 56%.

Workup

  1. temperatureheated further for 3-6 h
  2. customWater was removed from the reaction azeotropically
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. washThe organic phase was washed with a 5% Na2CO3 solution
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. distillationdistilled further

Sources & evidence

ORD record
ord-3f9a1549855c4b0584c8073fd88b0155
Source dataset
uspto-grants-2015_11
Patent number
US09187709B2

Reaction notes

Loading…