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

HRID 1579603Notes

Reaction equation

HRID 1579603 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:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Cl.Cl>N1C=CC=CC=1>[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][S:10][C:3]1[C:4](=[O:9])[O:5][C:6]([CH3:8])=[CH:7][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 99743-Fluorobenzyl chlorideHCID 547312374-Hydroxy-3-mercapto-6-methyl-2-pyrone

Product 1

HCID 547276663-(m-Fluorobenzylthio)-4-hydroxy-6-methyl-2-pyroneYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

4-Hydroxy-3-mercapto-6-methyl-2-pyrone (50 g., 0.317 mole) and m-fluorobenzylchloride (45.8 g., 0.317 mole) were dissolved in pyridine (250 ml.). The temperature rose from 20° to 36°C. The resulting solution was heated at 90°C. for two hours and poured over ice and 500 ml. of concd. hydrochloric acid. This mixture was extracted with methylene chloride. The extract was dried (MgSO4) and the solvent removed by evaporation. The residue was mixed with hexane, filtered and dried, yielding 44.6 g. (53 percent) of the desired product. Recrystallization from benzene gave the pure product as a white solid, m.p. 123.5°-124°C.

Workup

  1. customrose from 20° to 36°C
  2. additionpoured over ice and 500 ml
  3. extractionThis mixture was extracted with methylene chloride
  4. dry with materialThe extract was dried (MgSO4)
  5. customthe solvent removed by evaporation
  6. additionThe residue was mixed with hexane
  7. filtrationfiltered
  8. customdried
  9. customyielding 44.6 g

Sources & evidence

ORD record
ord-0d868a8e36e44b2fa65b648ac17d877f
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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