Methanesulfenylchloride → HCID 54725953, compound

HRID 1579573Notes

Reaction equation

HRID 1579573 reaction equation
[CH3:1][S:2]Cl.[Na].[OH:5][C:6]1[CH:11]=[C:10]([CH3:12])[O:9][C:8](=[O:13])[CH:7]=1>C(Cl)Cl>[OH:5][C:6]1[CH:11]=[C:10]([CH3:12])[O:9][C:8](=[O:13])[C:7]=1[S:2][CH3:1]

Participants

5

Reactant 3

HCID 138595MethanesulfenylchlorideHCID 5360545SodiumHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54725953HCID 54725953, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Methanesulfenyl chloride (21.6 g., 0.261 mol) dissolved in methylene chloride (100 ml.) was added to a rapidly stirred slurry of the monosodium salt of 4-hydroxy-6-methyl-2-pyrone (38.6 g., 0.261 mol) in methylene chloride (500 ml.) over a period of 35 minutes. The reaction temperature was maintained at 25°C. with cooling during the addition; then stirring was continued at ambient temperature for 4 hours. The methylene chloride was removed by distillation in vacuo and the residue triturated with water (200 ml.) to remove the by-product sodium chloride. The crude product was removed by filtration, 26.0 g., m. 127°-134°C., 58 percent yield; after recrystallization from 2-propanol, 17.2 g., m. 139°-140.5°C., 38 percent yield

Workup

  1. temperaturewith cooling during the addition
  2. customThe methylene chloride was removed by distillation in vacuo
  3. customthe residue triturated with water (200 ml.)
  4. customto remove the by-product sodium chloride
  5. customThe crude product was removed by filtration, 26.0 g
  6. custom127°-134°C., 58 percent yield
  7. customafter recrystallization from 2-propanol, 17.2 g
  8. custom139°-140.5°C., 38 percent yield

Sources & evidence

ORD record
ord-cd81bbbaf7ec4be281b9ccb990abd521
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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