1-Butanol → Butyl methanesulfonate

HRID 1835912Notes

Reaction equation

HRID 1835912 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>ClCCl>[CH3:13][S:14]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 15953Butyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 500 cm3 round-bottomed flask, equipped with a magnetic stirrer and pressure equalising dropping funnel, was added butanol (55,6 g, 0.75 mol), triethylamine (55.7 g, 0.55 mol) and dichloromethane (300 cm3). Methanesulfonyl chloride (57.3 g, 0.05 mol) was then added dropwise over a two-hour period from the dropping funnel, with cooling from an ice bath. The mixture was stirred for a further 24 hours at room temperature. The reaction mixture was filtered, concentrated on a rotary evaporator, and distilled (bp −80−90° C. at 5 mm Hg). This gave 68.1 g (98%) of a colourless oil.

Workup

  1. customTo a 500 cm3 round-bottomed flask, equipped with a magnetic stirrer
  2. temperaturewith cooling from an ice bath
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated on a rotary evaporator
  5. distillationdistilled (bp −80−90° C. at 5 mm Hg)

Sources & evidence

ORD record
ord-7372138ac66f4e1c8c9d25fc278b9d79
Source dataset
uspto-grants-2004_08
Patent number
US06774240B2

Reaction notes

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