Water → HCID 123534788, compound

HRID 926683Notes

Reaction equation

HRID 926683 reaction equation
[CH3:1][C:2]1(O)[CH:13]2[CH2:14][O:15][CH2:16][CH:12]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:13]2[CH2:14][O:15][CH2:16][CH:12]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117902425HCID 117902425, compound

Product 1

HCID 123534788HCID 123534788, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Crude 4-methyl-dodecahydro-2-oxa-cyclopentacyclododecen-4-ol (133 g) from Step 3 was dissolved in toluene (1 L). p-Toluenesulfonic acid (pTSA) (4 g) was added and the reaction was heated to reflux with a water trap. After 8 hours, there was no more water separated. The reaction was cooled and washed with sodium carbonate solution. Further distillation afforded 13-methyl-3a,4,5,6,7,8,9,10,11,13a-decahydro-1H,3H-2-oxa-cyclopentacyclododecene (101 g, ˜82% yield).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux with a water trap
  3. customseparated
  4. temperatureThe reaction was cooled
  5. washwashed with sodium carbonate solution
  6. distillationFurther distillation

Sources & evidence

ORD record
ord-54eaf0ac0d164c8baffec79bd31368c5
Source dataset
uspto-grants-2016_03
Patent number
US09289366B2

Reaction notes

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