Sulfuric Acid → 1,3-Adamantanediol

HRID 1978108Notes

Reaction equation

HRID 1978108 reaction equation
S(=O)(=O)(O)[OH:2].[OH:6][C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2>>[OH:6][C:7]12[CH2:8][CH:9]3[CH2:15][CH:13]([CH2:12][C:11]([OH:2])([CH2:10]3)[CH2:16]1)[CH2:14]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 641521-Adamantanol

Product 1

HCID 5738291,3-Adamantanediol

Procedure

To 324 ml of 70% sulfuric acid was added 0.33 mole of the 1-hydroxyadamantane obtained in Comparative Example 5, and the resultant mixture was stirred at the temperature of 95° C. for 4 hours. The reaction product was poured into ice water extracted with ethanol. The water phase was neutralized by sodium hydroxide and extracted with n-butanol, then the solvent was distilled off from the extract under reduced pressure. The crude product was recrystallized from n-hexane to obtain a powderly 1,3-dihydroxyadamantane.

Workup

  1. customobtained in Comparative Example 5
  2. extractionextracted with ethanol
  3. extractionextracted with n-butanol
  4. distillationthe solvent was distilled off from the
  5. extractionextract under reduced pressure
  6. customThe crude product was recrystallized from n-hexane

Sources & evidence

ORD record
ord-ac8c5faf3d6c49f7ac076a271e02dfcc
Source dataset
uspto-grants-2001_05
Patent number
US06235851B1

Reaction notes

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