p-Toluenesulfonic acid → 1253785-23-7

HRID 874764Notes

Reaction equation

HRID 874764 reaction equation
[CH3:1][CH:2]1[CH:13]=[C:12]([CH3:14])[CH2:11][CH2:10][C:3]21[CH:8]([OH:9])[O:7][CH2:6][CH2:5][CH2:4]2.[CH3:15]C1C=CC(S(O)(=O)=O)=CC=1>CO.CC(OC)(C)C>[CH3:15][O:9][CH:8]1[C:3]2([CH2:10][CH2:11][C:12]([CH3:14])=[CH:13][CH:2]2[CH3:1])[CH2:4][CH2:5][CH2:6][O:7]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66600327HCID 66600327, compound

Product 1

HCID 666007061253785-23-7Yield 7,041.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 7,9-dimethyl-2-oxaspiro[5.5]undec-8-en-1-ol (5.0 g, 26 mmol) and p-TsOH (50 mg) in methanol (20 ml) was stirred at reflux temperature for 0.5 hours. The mixture was diluted with MTBE, washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled bulb-to-bulb to yield a colorless oil (4.3 g, 80%).

Workup

  1. temperatureat reflux temperature for 0.5 hours
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. distillationThe residue was distilled bulb-to-bulb

Sources & evidence

ORD record
ord-0c9fd9ac2bf1467da2db150daf4fc3f1
Source dataset
uspto-grants-2015_03
Patent number
US08980943B2

Reaction notes

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