1-Butanol → Butyl methanesulfonate

HRID 1295706Notes

Reaction equation

HRID 1295706 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([OH:10])[CH2:7][CH2:8][CH3:9].C(N(CC)CC)C.ClCCl>O>[CH2:6]([O:10][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 15953Butyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulfonyl chloride (15.45 g, 0.13 mol) was added to a mixture of n-butanol (10 g, 0.13 mol), triethylamine (26.3 g, 0.26 mol) and dichloromethane (150 g) at 10° C. After being stirred at room temperature overnight, water (100 g) was added to the reaction mixture and the layers were separated. The organic layer was concentrated in vacuo at room temperature. This gave 18 g (90%) of the title mesylate as an oil. 1H NMR analysis supports the stated structure. *Previously described in J. Am. Chem. Soc. 1933, 55, 345-349.

Workup

  1. customthe layers were separated
  2. concentrationThe organic layer was concentrated in vacuo at room temperature

Sources & evidence

ORD record
ord-6639ac8416e34247b0f60ab0674711b8
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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