Acetic Anhydride → 1,3,5-Adamantanetriol

HRID 431417

Reaction equation

HRID 431417 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([OH:12])([CH2:5]3)[CH2:3]1)[CH2:9]2.C(OC(=O)C)(=[O:15])C.OC12CC3CC(CC(C3)C1)C2>>[OH:1][C:2]12[CH2:11][C:6]3([OH:15])[CH2:7][CH:8]([CH2:10][C:4]([OH:12])([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 641521-AdamantanolHCID 5738291,3-Adamantanediol

Product 1

HCID 98990221,3,5-Adamantanetriol

Procedure

One mol of 1,3-dihydroxyadamantane was stirred in an acetic acid-acetic anhydride solution of CrO3, oxidizing agent, with heating. After carrying out the reaction for 8 hours, the reaction solution was neutralized to obtain a mixture of polyhydroxylated compounds of hydroxyadamantane. This mixture was partitioned by high performance liquid chromatography to obtain 1,3,5-trihydroxyadamantane.

Workup

  1. temperaturewith heating
  2. customthe reaction for 8 hours
  3. customto obtain
  4. customThis mixture was partitioned by high performance liquid chromatography

Sources & evidence

ORD record
ord-ca0613a1e0fc4d14b7ede5c9f6165983
Source dataset
uspto-grants-2003_12
Patent number
US06660450B2

Linked notes

Loading…