Isopropanol → Ethanesulfonic acid, isopropyl ester

HRID 332585Notes

Reaction equation

HRID 332585 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 mL), 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-fe7ec1ca54c849fe9a96f665ff7ccbf3
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Reaction notes

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