Hydrochloric Acid → 3-(p-Fluorobenzylthio)-4-hydroxy-6-methyl-2-pyrone

HRID 1579583Notes

Reaction equation

HRID 1579583 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[SH:10].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.Cl>N1C=CC=CC=1>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][S:10][C:3]2[C:4](=[O:9])[O:5][C:6]([CH3:8])=[CH:7][C:2]=2[OH:1])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 96024-Fluorobenzyl chlorideHCID 547312374-Hydroxy-3-mercapto-6-methyl-2-pyrone

Product 1

HCID 547358903-(p-Fluorobenzylthio)-4-hydroxy-6-methyl-2-pyrone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 10.5 g. (0.0664 mole) of 4-hydroxy-6-methyl-3-mercapto-2-pyrone in 50 ml. of pyridine was added 9.60 g. (0.0664 mole) of p-fluorobenzyl chloride in one portion. The reaction was slightly exothermic, the temperature rising from 25° to 34°C. The reaction mixture was then allowed to stand at room temperature for four hours and at the end of this period was poured into a mixture of ice and 100 ml. of concentrated hydrochloric acid. The gummy precipitate was extracted with methylene chloride and the extract dried over anhydrous magnesium sulfate. The solvent was removed by evaporation in vacuo, leaving a light yellow oil, which crystallized upon cooling, weight 12.5 g. (71 percent). This was recrystallized from a solvent system of methylcyclohexane, benzene and ethanol to give light yellow crystals, m.p. 114.5°-118.5°C.; weight 7.20 g. Recrystallization from benzene gave the pure 3-(p-fluorobenzylthio)-4-hydroxy-6-methyl-2-pyrone as a pale yellow, crystalline solid, m.p. 118°-122°C.

Workup

  1. customrising from 25° to 34°C
  2. additionwas poured into a mixture of ice and 100 ml
  3. extractionThe gummy precipitate was extracted with methylene chloride
  4. dry with materialthe extract dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation in vacuo
  6. customleaving a light yellow oil, which
  7. customcrystallized
  8. temperatureupon cooling
  9. customThis was recrystallized from a solvent system of methylcyclohexane, benzene and ethanol
  10. customto give light yellow crystals, m.p. 114.5°-118.5°C.
  11. customRecrystallization from benzene

Sources & evidence

ORD record
ord-2c96222f9507467aa1a9a373ff1b98aa
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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