2-Ethyl-1-butanol → Toluene-4-sulfonic acid 2-ethylbutyl ester

HRID 1509856Notes

Reaction equation

HRID 1509856 reaction equation
[CH2:1]([CH:3]([CH2:6][CH3:7])[CH2:4][OH:5])[CH3:2].C1N2CCN(CC2)C1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl>[CH2:1]([CH:3]([CH2:6][CH3:7])[CH2:4][O:5][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23])[CH3:2]

Participants

5

Reactant 3

HCID 73582-Ethyl-1-butanolHCID 73974-Toluenesulfonyl chlorideHCID 9237Dabco

Product 1

HCID 54473552Toluene-4-sulfonic acid 2-ethylbutyl esterYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-ethyl-1-butanol (1.00 g, 9.79 mmol), triethylenediamine (1.32 g, 11.7 mmol) in DCM (30 mL, 0.5 mol) cooled to 0° C. was added p-toluenesulfonyl chloride (1.96 g, 10.3 mmol) in DCM (10 mL) The reaction mixture was stirred for 30 min, and extracted with 1.0N NaOH (2×40 mL). The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and isolated by rotary evaporation to give the title compound (2.40 g).

Workup

  1. extractionextracted with 1.0N NaOH (2×40 mL)
  2. customThe organic layer was collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customisolated by rotary evaporation

Sources & evidence

ORD record
ord-c22cce2bcd214c5d86aab9e7c6c65491
Source dataset
uspto-grants-2012_07
Patent number
US08211894B2

Reaction notes

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