HCID 11116012, compound → HCID 54737969, compound

HRID 1579579Notes

Reaction equation

HRID 1579579 reaction equation
[CH:1]([S:4]Cl)([CH3:3])[CH3:2].[OH:6][C:7]1[CH:12]=[C:11]([CH3:13])[O:10][C:9](=[O:14])[CH:8]=1>C(Cl)Cl>[CH:1]([S:4][C:8]1[C:9](=[O:14])[O:10][C:11]([CH3:13])=[CH:12][C:7]=1[OH:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11116012HCID 11116012, compoundHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54737969HCID 54737969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 62.7 g. (0.57 mole) of isopropanesulfenyl chloride in 300 ml. of methylene chloride was added dropwise to a suspension of 84.5 g. (0.57 mole) of 4-hydroxy-6-methyl-2-pyrone in 200 ml. of methylene chloride while the reaction mixture was maintained at 20°C. The mixture was then warmed to 40°C. for 1.5 hours and finally stirred at room temperature for 17 hours. The by-product sodium chloride was removed by filtration and the filtrate evaporated to dryness, leaving a red liquid (85.5 g.) which solidified upon cooling in an ice bath. The crude product was recrystallized from cyclohexane to give 33.1 g. (28 percent) of the product as off-white crystals, m. 89°-91°C. A second recrystallization from cyclohexane gave white crystals, m. 91°-92°C.

Workup

  1. customThe by-product sodium chloride was removed by filtration
  2. customthe filtrate evaporated to dryness
  3. customleaving a red liquid (85.5 g.) which
  4. temperatureupon cooling in an ice bath
  5. customThe crude product was recrystallized from cyclohexane
  6. customto give 33.1 g
  7. custom89°-91°C
  8. customA second recrystallization from cyclohexane
  9. customgave white crystals, m
  10. custom91°-92°C.

Sources & evidence

ORD record
ord-cc56ea4b12e34b0284dbed3bd141a7a7
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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