4-Toluenesulfonyl chloride → 2-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol

HRID 237443Notes

Reaction equation

HRID 237443 reaction equation
[CH3:1][C:2]([OH:7])([CH3:6])[CH2:3][CH2:4][OH:5].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>ClCCl.N1C=CC=CC=1>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:5][CH2:4][CH2:3][C:2]([OH:7])([CH3:6])[CH3:1])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 247470Isopentyldiol

Product 1

HCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-methylbutane-1,3-diol (2.5 mL) in dichloromethane (30 mL) and pyridine (2.1 mL) is added at 0° C. p-toluene-sulfonylchloride (4.6 g) in portions. The mixture is stirred for 12 hours at room temperature, diluted with dichloromethane and washed with 1 M aqueous HCl solution and brine. After drying (MgSO4) the solvent is evaporated and the product is purified by chromatography on silica gel (cyclohexane/ethyl acetate 90:10→70:30) to give the title compound. Yield: 3.2 g; Mass spectrum (ESI+): m/z=276 [M+NH4]+.

Workup

  1. washwashed with 1 M aqueous HCl solution and brine
  2. dry with materialAfter drying (MgSO4) the solvent
  3. customis evaporated
  4. customthe product is purified by chromatography on silica gel (cyclohexane/ethyl acetate 90:10→70:30)

Sources & evidence

ORD record
ord-806d6d4232fe479eabfcec541b3fac8a
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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