p-Toluenesulfonic acid → tetradecahydrocyclododeca[b]furan

HRID 2198820Notes

Reaction equation

HRID 2198820 reaction equation
O[CH2:2][CH2:3][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].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:4]12[CH2:3][CH2:2][O:16][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 14687817HCID 14687817, compound

Product 1

HCID 14687820tetradecahydrocyclododeca[b]furanYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The toluene solution of the diol from step 5 (approximately 0.59 mol) was mixed with 12 gm of p-toluenesulfonic acid and heated with agitation for approximately 4 hours under a water separator. After the reaction was complete, the mixture was neutralized with 5% sodium hydroxide solution, the aqueous phase was separated, and the toluene phase was evaporated. Approximately 80 gm of 13-oxabicyclo[10.3.0]pentadecane (65% yield) were isolated by vacuum distillation at 90° to 95° C./0.25 mbar.

Workup

  1. temperatureheated with agitation for approximately 4 hours under a water separator
  2. customthe aqueous phase was separated
  3. customthe toluene phase was evaporated

Sources & evidence

ORD record
ord-715f7bb9de1245b5a040262c4b65bcb0
Source dataset
uspto-grants-1982_11
Patent number
US04360468

Reaction notes

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