Water → 2,2-Dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane methylsulphonate

HRID 704128

Reaction equation

HRID 704128 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1([CH3:17])[O:12][CH2:11][C:10]([CH2:15][CH3:16])([CH2:13][OH:14])[CH2:9][O:8]1.O>N1C=CC=CC=1>[CH3:1][S:2]([OH:4])(=[O:8])=[O:3].[CH3:6][C:7]1([CH3:17])[O:8][CH2:9][C:10]([CH2:15][CH3:16])([CH2:13][OH:14])[CH2:11][O:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 118161521,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-

Product 1

HCID 200755932,2-Dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane methylsulphonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (15 ml.) was added dropwise to a stirred solution of 2,2-dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane 1 (33.0 g) in dry pyridine (100 ml.) at 0°. The mixture was stirred for two hours at room temperature and then poured into water. The aqueous mixture was extracted with ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. 2,2-Dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane methane sulphonate was obtained as a colourless oil (39 g.) which solidified on standing. The compound was used without further purification.

Workup

  1. extractionThe aqueous mixture was extracted with ether
  2. washThe ethereal extracts were washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-8084b5d0d46c477d9685028d329a148e
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Linked notes

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