Sodium Chloride → HCID 54694326, compound

HRID 1579575Notes

Reaction equation

HRID 1579575 reaction equation
[C:1]1([S:7]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].[OH:10][C:11]1[CH:16]=[C:15]([CH3:17])[O:14][C:13](=[O:18])[CH:12]=1.[Cl-].[Na+]>C1C=CC=CC=1>[OH:10][C:11]1[CH:16]=[C:15]([CH3:17])[O:14][C:13](=[O:18])[C:12]=1[S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 5360545SodiumHCID 11008040Benzenesulfenyl chlorideHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54694326HCID 54694326, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Benzenesulfenyl chloride (7.2 g., 0.050 mol) dissolved in benzene (15 ml.) was added to a rapidly stirred slurry of the monosodium salt of 4-hydroxy-6-methyl-2-pyrone (7.4 g., 0.050 mol) in benzene (110 ml.) over a period of 12 minutes. The reaction temperature was maintained at 25°-27°C. with cooling during the addition; then the reaction mixture was heated at reflux for 30 minutes. The benzene was removed by distillation in vacuo and the residue triturated with water (100 ml.) to remove the by-product sodium chloride. The crude product was removed by filtration, 10.9 g., m. 158°-163°C., 93 percent yield. A portion was recrystallized from ethanol, m. 164.5°-165.5°C. Evaporation of the aqueous filtrate to dryness in vacuo produced 2.9 g. (100 percent yield) of the by-product sodium chloride.

Workup

  1. temperatureThe reaction temperature was maintained at 25°-27°C.
  2. temperaturewith cooling during the addition
  3. temperaturethen the reaction mixture was heated
  4. temperatureat reflux for 30 minutes
  5. customThe benzene was removed by distillation in vacuo
  6. customthe residue triturated with water (100 ml.)
  7. customto remove the by-product sodium chloride
  8. customThe crude product was removed by filtration, 10.9 g
  9. custom158°-163°C., 93 percent yield
  10. customA portion was recrystallized from ethanol, m
  11. custom164.5°-165.5°C
  12. customEvaporation of the aqueous filtrate to dryness in vacuo
  13. customproduced 2.9 g

Sources & evidence

ORD record
ord-030d056da4a1430d932efa7c44b0137d
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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