Hydrochloric Acid → HCID 54731453, compound

HRID 1579578Notes

Reaction equation

HRID 1579578 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[CH:3]=1.[CH2:10]([S:12]Cl)[CH3:11].Cl>C1(C)C=CC=CC=1>[CH2:10]([S:12][C:3]1[C:4](=[O:9])[O:5][C:6]([CH3:8])=[CH:7][C:2]=1[OH:1])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12275523ethanesulfenyl chlorideHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54731453HCID 54731453, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 37.2 g. (0.295 mole) of 4-hydroxy-6-methyl-2-pyrone and 28.4 g. (0.295 mole) of ethanesulfenyl chloride in 900 ml. of toluene was heated under reflux with stirring at 75°C. for two hours, during which time hydrogen chloride evolved. The reaction mixture was cooled to room temperature and filtered to remove 24.2 g. of a solid (m. 170°-172°C. - probably a mixture of starting pyrone and an unknown substance). The filtrate was concentrated to give 13.3 g. (25 percent) of the product as a white solid, m. 94°-95°C. Recrystallization from cyclohexane gave the pure product as white crystals, m. 101°-102°C.

Workup

  1. additionA mixture of 37.2 g
  2. temperatureunder reflux
  3. filtrationfiltered
  4. customto remove 24.2 g
  5. addition170°-172°C. - probably a mixture of starting pyrone
  6. concentrationThe filtrate was concentrated
  7. customto give 13.3 g
  8. custom94°-95°C
  9. customRecrystallization from cyclohexane

Sources & evidence

ORD record
ord-6e017573ea894c669703f33b7b5e3f89
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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