Hydrochloric Acid → HCID 54729468, compound

HRID 1579584Notes

Reaction equation

HRID 1579584 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[SH:10].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>N1C=CC=CC=1>[CH2:11]([S:10][C:3]1[C:4](=[O:9])[O:5][C:6]([CH3:8])=[CH:7][C:2]=1[OH:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 547312374-Hydroxy-3-mercapto-6-methyl-2-pyrone

Product 1

HCID 54729468HCID 54729468, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 8.0 g. (0.051 mole) of 4-hydroxy-3-mercapto-6-methyl-2-pyrone in 38 ml. of pyridine was added 6.4 g. (0.051 mole) of benzyl chloride portionwise with stirring at room temperature. The reaction was slightly exothermic, the temperature rising from 23° to 30°C. The reaction mixture was stirred at room temperature for 30 minutes, and then heated on the steam bath for one hour at 90°-95°C. The reaction mixture was then cooled to room temperature and poured into a mixture of ice and 80 ml. of concentrated hydrochloric acid. The gummy precipitate, thus formed, was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, filtered and evaporated to dryness to give 7.7 g. (61%) of brown oil, which was crystallized from toluene, containing a little methylcyclohexane, to give 5.0 g. of yellow-brown crystals, m.p. 117°-126°C. Recrystallization of this substance from toluene gave the pure 3-benzylthio-4hydroxy-6-methyl-2-pyrone as cream colored crystals, m.p. 127.5°-128.5°C.

Workup

  1. customrising from 23° to 30°C
  2. temperatureheated on the steam bath for one hour at 90°-95°C
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. additionpoured into a mixture of ice and 80 ml
  5. customThe gummy precipitate, thus formed
  6. extractionwas extracted with methylene chloride
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customto give 7.7 g
  11. custom(61%) of brown oil, which was crystallized from toluene
  12. additioncontaining a little methylcyclohexane
  13. customto give 5.0 g
  14. customRecrystallization of this substance from toluene

Sources & evidence

ORD record
ord-0ed5a6d992eb49ae8139bd55c205b905
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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