4-Toluenesulfonyl chloride → 1-Methoxybutan-2-yl 4-methylbenzene-1-sulfonate

HRID 2206004Notes

Reaction equation

HRID 2206004 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([OH:7])[CH2:5][CH3:6].[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:7][CH:4]([CH2:5][CH3:6])[CH2:3][O:2][CH3:1])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 408952-Butanol, 1-methoxy-

Product 1

HCID 127007761-Methoxybutan-2-yl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 1-methoxybutan-2-ol (1.10 mL) in pyridine (5 mL) was added dropwise a solution of 4-methylbenzenesulfonyl chloride (2.75 g) in pyridine (15 mL) over 30 min or more at 0° C. The reaction mixture was stirred overnight at room temperature, and poured into ice-water. The reaction mixture was stirred at 0° C. for 1 hr, and the precipitate was collected by filtration, and washed with cold water. The obtained solid was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.23 g).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 1 hr
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with cold water
  4. customThe obtained solid was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3905931a783b46d2bfcc6347ed8e3d0a
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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