Hydrochloric Acid → 2-Acetyl-2-methylpropane-1,3-diol bismethanesulphonate

HRID 1649174Notes

Reaction equation

HRID 1649174 reaction equation
[O:1]=[C:2]([CH3:9])[C:3]([CH2:7][OH:8])([CH2:5][OH:6])[CH3:4].[CH3:10][S:11](Cl)(=[O:13])=[O:12].N1C=CC=CC=1.Cl>ClCCCl>[CH3:10][S:11]([O:6][CH2:5][C:3]([C:2](=[O:1])[CH3:9])([CH3:4])[CH2:7][O:8][S:11]([CH3:10])(=[O:13])=[O:12])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 5365163,3-Bis(hydroxymethyl)-2-butanone

Product 1

HCID 47373912-Acetyl-2-methylpropane-1,3-diol bismethanesulphonateYield 70%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

66 g (0.5 mol) of 3-oxo-2,2-bis-(hydroxymethyl)butane (for the preparation, see Beilstein H 1, E III 3306, IV 4132 and J. Chem. Soc., London, 1932, 2671) were dissolved in 300 ml of 1,2-dichlorethane, 114.5 g (1 mol) of methanesulphonyl chloride were added dropwise, and 158 g (2 mol) of pyridine were added dropwise at 0°-5° C. The mixture was subsequently stirred at room temperature for 15 hours and then poured onto 600 ml of ice-water and 100 ml of concentrated hydrochloric acid. A solid thereby precipitated and was filtered off. The aqueous phase was extracted with 1,000 ml of methylene chloride; the solid was dissolved in the methylene chloride phase, the organic phase was dried over sodium sulphate, the solvent was distilled off under a waterpump vacuum and the residue was suspended in 200 ml of ether. The residue was filtered off and washed with 100 ml of ether. 100 g (about 70% of theory) of 2-acetyl-2-methyl-propane-1,3-diol bismethanesulphonate of melting point 105°-108° C. were obtained. ##STR71##

Workup

  1. customA solid thereby precipitated
  2. filtrationwas filtered off
  3. extractionThe aqueous phase was extracted with 1,000 ml of methylene chloride
  4. dissolutionthe solid was dissolved in the methylene chloride phase
  5. dry with materialthe organic phase was dried over sodium sulphate
  6. distillationthe solvent was distilled off under a waterpump vacuum
  7. filtrationThe residue was filtered off
  8. washwashed with 100 ml of ether

Sources & evidence

ORD record
ord-a6b78a399d564eae973646d1ac90949b
Source dataset
uspto-grants-1983_11
Patent number
US04415586

Reaction notes

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