Methanesulfonyl chloride → HCID 20189890, compound

HRID 1788640Notes

Reaction equation

HRID 1788640 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][OH:11]>N1C=CC=CC=1.O>[CH3:1][S:2]([O:11][CH2:10][CH2:9][CH:8]([CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:12][CH2:13][CH3:14])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 125082552-Propylbutane-1,4-diol

Product 1

HCID 20189890HCID 20189890, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulphonyl chloride (16.95 g) was added dropwise to a stirred solution of 3-hydroxymethylhexan-1-ol (8.94 g) in pyridine (39.5 g), maintaining the temperature at less than 5° C. Following the addition, the reaction mixture was stirred at 0° C. for 1.5 hours, then diluted with water and extracted with dichloromethane. The extracts were washed successively with water, dilute hydrochloric acid (X 2), water, aqueous sodium bicarbonate, and water, then dried over magnesium sulphate and concentrated to give 3-methanesulphonyloxymethylhex-1-yl methanesulphonate. (16.13 g, 83%) as a yellow oil.

Workup

  1. temperaturemaintaining the temperature at less than 5° C
  2. additionthe addition
  3. extractionextracted with dichloromethane
  4. washThe extracts were washed successively with water, dilute hydrochloric acid (X 2), water, aqueous sodium bicarbonate, and water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b735e5a5475e4b5385211bc2dd514f1b
Source dataset
uspto-grants-1987_08
Patent number
US04684396

Reaction notes

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