Methanesulfonyl chloride → 2-Ethyl-2-(mesyloxymethyl)hexanal

HRID 2229501Notes

Reaction equation

HRID 2229501 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([C:8]([CH2:15][OH:16])([CH2:11][CH2:12][CH2:13][CH3:14])[CH:9]=[O:10])[CH3:7]>>[CH2:6]([C:8]([CH2:15][O:16][S:2]([CH3:1])(=[O:4])=[O:3])([CH2:11][CH2:12][CH2:13][CH3:14])[CH:9]=[O:10])[CH3:7]

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 125384672-Ethyl 2-(hydroxymethyl)hexanal

Product 1

HCID 115722172-Ethyl-2-(mesyloxymethyl)hexanalYield 103.4%

Procedure

To a cold (10° C.) solution of 12.6 g (0.11 mole) of methanesulfonyl chloride and 10.3 g (0.13 mole) of triethylemine was added dropwise 15.8 g of 2-ethyl-2-(hydroxymethyl)hexanal, prepared according to the procedure described in Chem. Ber. 98, 728-734 (1965), while maintaining the reaction temperature below 30° C. The reaction mixture was stirred at room temperature for 18 h, quenched with dilute HCl and extracted with methlyene chloride. The methylene chloride extract was dried over MgSO4 and concentrated in vacuo to give 24.4 g of brown oil.

Workup

  1. customprepared
  2. temperature98, 728-734 (1965), while maintaining the reaction temperature below 30° C
  3. customquenched with dilute HCl
  4. extractionextracted with methlyene chloride
  5. extractionThe methylene chloride extract
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72d82efed2474f4280b054c68ad9c8e1
Source dataset
uspto-grants-2002_07
Patent number
US06420417B1

Reaction notes

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