Hydrochloric Acid → Cyclobutyl 4-methylbenzene-1-sulfonate

HRID 1919865Notes

Reaction equation

HRID 1919865 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[C:6]1([CH3:16])[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1.Cl>N1C=CC=CC=1>[CH3:16][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 76218Cyclobutanol

Product 1

HCID 12621595Cyclobutyl 4-methylbenzene-1-sulfonateYield 65.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of cyclobutanol (1 g, 13.9 mmol) in pyridine (20 mL) was added p-toluenesulfonyl chloride (2.9 g, 15.3 mmol) and the solution stirred at room temperature for 4 hours. Aqueous HCl was then added, and the solution extracted with ethyl acetate (×3). The combined organic layers were washed successively with saturated aqueous copper(II) sulfate (×3) and brine, then dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue was purified using flash column chromatography on silica gel (gradient of 0% to 5% ethyl acetate in petrol) to give cyclobutyl 4-methylbenzenesulfonate (2.05 g, 9.07 mmol, 65%) as a colourless oil.

Workup

  1. extractionthe solution extracted with ethyl acetate (×3)
  2. washThe combined organic layers were washed successively with saturated aqueous copper(II) sulfate (×3) and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-1ab4e9bebf764f79a84365b0e41b6b33
Source dataset
uspto-grants-2012_05
Patent number
US08168673B2

Reaction notes

Loading…