Hydrochloric Acid → 4-Hydroxy-6-methyl-3-(1-naphthylmethylthio)-2-pyrone

HRID 1579581Notes

Reaction equation

HRID 1579581 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[SH:10].Cl[CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.Cl>N1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[S:10][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68451-ChloromethylnaphthaleneHCID 547312374-Hydroxy-3-mercapto-6-methyl-2-pyrone

Product 1

HCID 547296884-Hydroxy-6-methyl-3-(1-naphthylmethylthio)-2-pyrone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 15.8 g. (0.100 mole) of 4-hydroxy-3-mercapto-6-methyl-2-pyrone in 100 ml. of pyridine was cooled in an ice bath to about 15°C., and 17.7 g. (0.100 mole) of 1-chloromethylnaphthalene was added in one portion. The flask was then heated at 90°-95°C. on the steam plate for four hours. The reaction mixture was cooled and poured into 200 ml. of concentrated hydrochloric acid and about 400 g. of ice. A gummy solid was formed and was extracted with methylene chloride. The wet extract was treated with Darco and dried over anhydrous sodium sulfate. The solvent was removed by evaporation in vacuo, leaving a brown gum, which was crystallized (Darco) from ethanol to give 9.8 g. (33 percent) of tan crystals m.p. 155.5°-157.5°C. Recrystallization from ethanol gave the pure 4-hydroxy-6-methyl-3-(1-naphthylmethylthio)-2-pyrone as cream colored crystals, m.p. 169.5°-170.5°C.

Workup

  1. temperatureThe flask was then heated at 90°-95°C. on the steam plate for four hours
  2. temperatureThe reaction mixture was cooled
  3. additionpoured into 200 ml
  4. customA gummy solid was formed
  5. extractionwas extracted with methylene chloride
  6. extractionThe wet extract
  7. additionwas treated with Darco
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed by evaporation in vacuo
  10. customleaving a brown gum, which
  11. customwas crystallized (Darco) from ethanol
  12. customto give 9.8 g
  13. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-c89bfdc87ea9432a893691608b3cc20f
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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