4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 4-methoxy-butyl ester

HRID 880515

Reaction equation

HRID 880515 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>ClCCl>[CH3:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 81071-Butanol, 4-methoxy-HCID 8471Triethylamine

Product 1

HCID 86601716Toluene-4-sulfonic acid 4-methoxy-butyl esterYield 32.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.91 g, 28.86 mmol) was added to the stirred solution of 4-methoxy-1-butanol (1.00 g, 9.62 mmol) in dichloromethane (15 mL) at 0° C. and stirred for 15 min. p-Toluene sulfonyl chloride (1.83 g, 9.62 mmol) was added and the mixture was warmed to ambient temperature and stirred for 2 h. The reaction mixture was quenched with ice-water and the organic layer was separated. The aqueous layer was extracted with dichloromethane (3×5 mL) and the combined organic layers were washed with saturated sodium bicarbonate, water, and brine; dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was purified by column chromatography over silica gel (60-120 mesh) with 0% to 20% ethyl acetate in petroleum ether as eluent to afford 4-methoxybutyl-4-methylbenzenesulfonate (800 mg, 32%) as a liquid.

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with ice-water
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with dichloromethane (3×5 mL)
  5. washthe combined organic layers were washed with saturated sodium bicarbonate, water, and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography over silica gel (60-120 mesh) with 0% to 20% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-e4ea53b126a146a2bc139d5c7719defe
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Linked notes

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