Acetic Anhydride → 1,3,5-Adamantanetriol

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

Reactant 3

HCID 7918Acetic Anhydride

HCID 641521-Adamantanol

HCID 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

temperaturewith heating
customthe reaction for 8 hours
customto obtain
customThis mixture was partitioned by high performance liquid chromatography

Sources & evidence

ORD record: ord-ca0613a1e0fc4d14b7ede5c9f6165983
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660450B2

Reaction notes

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