4-Toluenesulfonyl chloride → Cyclohexyl p-toluenesulfonate

HRID 909966Notes

Reaction equation

HRID 909966 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N12CCN(CC1)CC2.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>C(OCC)(=O)C>[CH:1]1([O:7][S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 7966CyclohexanolHCID 9237Dabco

Product 1

HCID 13722Cyclohexyl p-toluenesulfonateYield 90.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

5.0 g (0.05 mol) cyclohexanol and 11.2 g (0.1 mol) 1,4-diazabicyclo[2.2.2]octane are added to 50 mL ethyl acetate. This solution is cooled in an ice bath and 14.3 g (0.075 mol) tosyl chloride in 30 ml ethyl acetate is added drop-wise over 15 minutes. The ice bath is removed and the mixture is allowed to stir at room temperature for 4 days. After this time the solid precipitate is filtered and washed. The ethyl acetate filtrate and washings are then combined and washed successively with 10% HCl, saturated aq NaHCO3 and brine. The ethyl acetate is then evaporated and the resulting oil is purified by column chromatography to yield 11.5 g (90%) of cyclohexyl-p-toluenesulfonate.

Workup

  1. temperatureThis solution is cooled in an ice bath
  2. customThe ice bath is removed
  3. filtrationAfter this time the solid precipitate is filtered
  4. washwashed
  5. washwashed successively with 10% HCl, saturated aq NaHCO3 and brine
  6. customThe ethyl acetate is then evaporated
  7. customthe resulting oil is purified by column chromatography

Sources & evidence

ORD record
ord-6315cfb6809c4fa99f05c997d6088221
Source dataset
uspto-grants-2011_09
Patent number
US08021820B2

Reaction notes

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