4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-cyclopropyl-ethyl ester

HRID 1985634Notes

Reaction equation

HRID 1985634 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH:12]1([CH2:15][CH2:16][OH:17])[CH2:14][CH2:13]1>N1C=CC=CC=1.ClCCl.CCOCC>[CH:12]1([CH2:15][CH2:16][O:17][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:14][CH2:13]1

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1376422-Cyclopropylethan-1-ol

Product 1

HCID 13568392Toluene-4-sulfonic acid 2-cyclopropyl-ethyl esterYield 89.2%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulfonyl chloride (7.20 g, 37.8 mmol) was added to a cooled (0° C.) solution of 2-cyclopropylethanol (4.00 g, 46.4 mmol) in pyridine (10 mL) and dichloromethane (60 mL). The reaction mixture was stirred at room temperature overnight, then diluted with ether (200 mL) and washed sequentially with water, 10% HCl, water and brine and then dried over anhydrous Na2SO4. Toluene-4-sulfonic acid 2-cyclopropylethyl ester (8.1 g, 89%) was obtained after removal of solvent and used for next step reaction without further purification.

Workup

  1. washwashed sequentially with water, 10% HCl, water and brine
  2. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-4f4cda14152441c1b170673e201a13af
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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