Isopropanol → Ethanesulfonic acid, isopropyl ester

HRID 517316Notes

Reaction equation

HRID 517316 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].C(N(CC)CC)C.[CH2:12]([S:14](Cl)(=[O:16])=[O:15])[CH3:13]>ClCCl>[CH:2]([O:4][S:14]([CH2:12][CH3:13])(=[O:16])=[O:15])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8471TriethylamineHCID 11667Ethanesulfonyl chloride

Product 1

HCID 134677Ethanesulfonic acid, isopropyl esterYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-propanol (2.4 mL, 32 mmol) in dichloromethane (50 were added triethylamine (3.5 ml, 25 mmol) and ethanesulfonyl chloride (2.0 mL, 21 mmol), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (2.4 g, 16 mmol, 75%).

Workup

  1. washThe reaction mixture was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  2. dry with materialdried over sodium sulfate
  3. filtrationThe drying agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cb4a978c837b473482650b11c320d99b
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Reaction notes

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