Isobutanol → 2-Methylpropyl methanesulfonate

HRID 616914Notes

Reaction equation

HRID 616914 reaction equation
[CH2:1]([OH:5])[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>ClCCl>[CH3:13][S:14]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 1192402-Methylpropyl methanesulfonateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cooled solution of 37 g (46.1 ml, 0.5 mol) of isobutyl alcohol and 75.75 g (104.3 ml, 0.75 mol) of triethylamine in 1800 ml of dichloromethane is added dropwise 63 g (42.57 ml, 0.55 mol) of methanesulfonyl chloride. The temperature of the reaction mixture during the addition is ca. 10°. The reaction mixture is then stirred for 1.5 hours at 10°. The reaction mixture is then diluted with dichloromethane, washed with ice water, cold 10% HCl, saturated KHCO3, saturated NaCl and dried (MgSO4). Solvent is removed in vacuo to yield 68 g (90%) of the isobutyl methanesulfonate as an oil.

Workup

  1. additionThe temperature of the reaction mixture during the addition
  2. customis ca. 10°
  3. washwashed with ice water, cold 10% HCl, saturated KHCO3, saturated NaCl
  4. dry with materialdried (MgSO4)
  5. customSolvent is removed in vacuo

Sources & evidence

ORD record
ord-928ce1d489e445a1bde4aef8f32af694
Source dataset
uspto-grants-1978_02
Patent number
US04076825

Reaction notes

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