S-Methyl methanethiosulfonate → HCID 54725953, compound

HRID 1579574Notes

Reaction equation

HRID 1579574 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[O:6][C:5](=[O:10])[CH:4]=1.[CH3:11][S:12]S(C)(=O)=O>C(O)C>[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[O:6][C:5](=[O:10])[C:4]=1[S:12][CH3:11]

Participants

5

Reactant 3

HCID 18064S-Methyl methanethiosulfonateHCID 5360545SodiumHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54725953HCID 54725953, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 47.0 g. (0.317 mole) of the monosodium salt of 4-hydroxy-6 -methyl-2-pyrone and 40.0 g. (0.317 mole) of methyl methanethiolsulfonate in 700 ml. of 2B absolute ethanol was heated under reflux with stirring for four hours. The solvent was then removed by evaporation in vacuo, leaving a viscous semi-solid. The crude substance was washed with water and extracted with methylene chloride. The combined extracts were dried over anhydrous sodium sulfate and evaporated in vacuo to dryness, leaving 24.8 g. of a yellow solid; which, when recrystallized from isopropanol gave 10.6 g. (20 percent) of the pure product m. 141.5°-143°C.

Workup

  1. additionA mixture of 47.0 g
  2. temperatureunder reflux
  3. customThe solvent was then removed by evaporation in vacuo
  4. customleaving a viscous semi-solid
  5. washThe crude substance was washed with water
  6. extractionextracted with methylene chloride
  7. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  8. customevaporated in vacuo to dryness
  9. customleaving 24.8 g
  10. customwhich, when recrystallized from isopropanol
  11. customgave 10.6 g
  12. custom141.5°-143°C.

Sources & evidence

ORD record
ord-92976254854c4278b92f2abb180f8b70
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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