4-Toluenesulfonyl chloride → Methyl p-toluenesulfonate

HRID 484280Notes

Reaction equation

HRID 484280 reaction equation
[O:1]1CCO[CH:2]1CC[C@H]1CC[C@H]([C@H]2CC[C@H](CO)CC2)CC1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>N1C=CC=CC=1.C(Cl)Cl>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([O:1][CH3:2])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 178520952HCID 178520952, compound

Product 1

HCID 6645Methyl p-toluenesulfonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.96 g of crude [trans-4-[trans-4-(2-(1,3-dioxolan-2-yl)ethyl)cyclohexyl]cyclohexyl]methanol in 20 ml of dry pyridine is treated at 0° C. with 2.1 g of p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 15 hours, then diluted with 200 ml methylene chloride and washed several times with water. The organic phase is fried over magnesium sulfate, filtered and evaporated. Chromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 1:9) gives [trans-4-]trans-4-(2-(1,3-dioxolan-2-yl)ethyl)cyclohexyl]cyclohexyl]methyl p-toluenesulfonate.

Workup

  1. washwashed several times with water
  2. filtrationfiltered
  3. customevaporated
  4. customChromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 1:9)

Sources & evidence

ORD record
ord-67df98f6805f4c2a9b7bee2773adc397
Source dataset
uspto-grants-1993_07
Patent number
US05230826

Reaction notes

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