Hydrochloric Acid → HCID 54710939, compound

HRID 1579577Notes

Reaction equation

HRID 1579577 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[O:6][C:5](=[O:10])[CH:4]=1.[ClH:11].[C:12]1(C)[CH:17]=[CH:16][C:15]([S:18](O)=O)=[CH:14][CH:13]=1>C(O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:4]2[C:5](=[O:10])[O:6][C:7]([CH3:9])=[CH:8][C:3]=2[OH:2])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10818p-Toluenesulfinic acidHCID 5360545SodiumHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54710939HCID 54710939, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the monosodium salt of 4-hydroxy-6-methyl-2-pyrone (29.6 g., 0.200 mol), p-chlorophenyl p-toluenethiolsulfonate (59.8 g., 0.200 mol), and 2B absolute ethanol (500 ml.) was heated at reflux with stirring for 6.5 hours. The ethanol was removed by distillation in vacuo and the residue triturated with water (300 ml.). The crude product was removed by filtration, 53.0 g. (m. 166°-177°C., 91% yield); after recrystallization from ethanol, 36.4 g., m. 175°-180°C., 68% yield. A second recrystallization produced the pure product, 18.0 g., m 181°-182°C., 34 percent yield. The aqueous filtrate was acidified with dilute HCl producing 21.8 g. (70 percent yield) of the by-product p-toluenesulfinic acid, m. 87°-89°C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe ethanol was removed by distillation in vacuo
  4. customthe residue triturated with water (300 ml.)
  5. customThe crude product was removed by filtration, 53.0 g
  6. custom(m. 166°-177°C., 91% yield)
  7. customafter recrystallization from ethanol, 36.4 g
  8. custom175°-180°C., 68% yield
  9. customA second recrystallization
  10. customproduced the pure product, 18.0 g
  11. customm 181°-182°C., 34 percent yield

Sources & evidence

ORD record
ord-a9c06b8630fc4a89a4b75024b3d7defc
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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