Sulfuric Acid → 3-(1-Adamantylthio)-4-hydroxy-6-methyl-2-pyrone

HRID 1579604Notes

Reaction equation

HRID 1579604 reaction equation
S(=O)(=O)(O)O.[C:6]12(O)[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.[OH:17][C:18]1[CH:23]=[C:22]([CH3:24])[O:21][C:20](=[O:25])[C:19]=1[SH:26]>>[C:6]12([S:26][C:19]3[C:20](=[O:25])[O:21][C:22]([CH3:24])=[CH:23][C:18]=3[OH:17])[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 641521-AdamantanolHCID 547312374-Hydroxy-3-mercapto-6-methyl-2-pyrone

Product 1

HCID 547361873-(1-Adamantylthio)-4-hydroxy-6-methyl-2-pyrone

Procedure

Ice (22 g.) was slowly added to 90 g. of concd. sulfuric acid with stirring, keeping the temperature below 35°C. by means of an ice-salt bath. 1-Adamantanol (18.2 g., 0.120 mole) was added followed by the slow addition of 15.8 g. (0.100 mole) of 4-hydroxy-3-mercapto-6-methyl-2-pyrone, keeping the temperature of the reaction mixture between 0° and 5°C. The ice bath was then removed from the reaction vessel, and the reaction mixture was warmed to 30°-40°C. with vigorous stirring for 1.5 hours. The mixture was then poured into ice water and allowed to stand for about 15 hours. The crude, solid product was collected on a filter, dried in vacuo over calcium chloride and recrystallized from ethanol (Darco) to give 8.3 g. (28 percent) of colorless needles, m.p. 175.5°-176.5°C. A second recrystallization from ethanol gave the pure product as colorless needles, m.p. 176°-177°C.

Workup

  1. customthe temperature below 35°C.
  2. additionfollowed by the slow addition of 15.8 g
  3. customthe temperature of the reaction mixture between 0° and 5°C
  4. customThe ice bath was then removed from the reaction vessel
  5. temperaturethe reaction mixture was warmed to 30°-40°C.
  6. additionThe mixture was then poured into ice water
  7. waitto stand for about 15 hours
  8. customThe crude, solid product was collected on a filter
  9. dry with materialdried in vacuo over calcium chloride
  10. customrecrystallized from ethanol (Darco)
  11. customto give 8.3 g
  12. customA second recrystallization from ethanol

Sources & evidence

ORD record
ord-02538ddda3864d96a3a3036be2d2ba1c
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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