Hydrochloric Acid → HCID 54725953, compound

HRID 1579572Notes

Reaction equation

HRID 1579572 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[O:6][C:5](=[O:10])[CH:4]=1.Cl.C1(C)C=C[C:15]([S:18](O)=O)=CC=1>C(O)C>[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[O:6][C:5](=[O:10])[C:4]=1[S:18][CH3:15]

Participants

6

Reactant 4

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

Product 1

HCID 54725953HCID 54725953, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the monosodium salt of 4-hydroxy- 6-methyl-2-pyrone (14.8 g., 0.100 mol), methyl p-toluenethiolsulfonate (20.2 g., 0.100 mol), and 2B absolute ethanol (250 ml.) was heated at reflux for 21 hours. The ethanol was removed by distillation in vacuo; on attempted trituration with water (200 ml.), an oil separated. The oil was removed and the aqueous phase extracted with chloroform (2 × 100 ml.). The oil and chloroform washings were combined, dried over anhydrous Na2SO4, and the chloroform removed by distillation in vacuo. The resulting solid product, 4.5 g. (m. 130°-136°C., 26% yield) was twice recrystallized from 2-propanol to obtain the pure product, m. 141°-141.5°. The aqueous layer was acidified with dilute HCl producing 10.0 g. (64 percent yield) of the by-product p-toluenesulfinic acid, m. 79°-85°C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 21 hours
  3. customThe ethanol was removed by distillation in vacuo
  4. customan oil separated
  5. customThe oil was removed
  6. extractionthe aqueous phase extracted with chloroform (2 × 100 ml.)
  7. dry with materialdried over anhydrous Na2SO4
  8. customthe chloroform removed by distillation in vacuo
  9. custom(m. 130°-136°C., 26% yield) was twice recrystallized from 2-propanol
  10. customto obtain the pure product, m
  11. custom141°-141.5°

Sources & evidence

ORD record
ord-e04cc4cc421548038f1d4e044d0fa647
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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