p-Toluenesulfonic acid → HCID 11085454, compound

HRID 2413361Notes

Reaction equation

HRID 2413361 reaction equation
[CH2:1]([CH:4]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[OH:16])[CH:2]=[CH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:3][CH:2]1[CH2:1][CH:4]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[O:16]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 20430924HCID 20430924, compound

Product 1

HCID 11085454HCID 11085454, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1 mole of 2-(2-propenyl)-cyclododecanol is dissolved, together with 20 g of p-toluenesulphonic acid, in 1000 ml of toluene, and the mixture is refluxed for 15 hours. The mixture is then neutralized with 10% sodium carbonate solution, the phases are separated and the organic phase is worked up by distillation. After the toluene has been drawn off, 14-methyl-13-oxabicyclo[10.3.0]pentadecane is obtained, in a yield of 98% of the theoretical yield, at a boiling range of from 85° to 88° C. at 0.05 torr. Colorless oil; scent: warm, vetiver-like sandalwood fragrance.

Workup

  1. temperaturethe mixture is refluxed for 15 hours
  2. customthe phases are separated
  3. distillationthe organic phase is worked up by distillation

Sources & evidence

ORD record
ord-9241a972fc484d83b182d61bda2050bc
Source dataset
uspto-grants-1985_01
Patent number
US04496748

Reaction notes

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