Acetic Acid → 5,7-Dimethyladamantane-1,3-diol

HRID 618986

Reaction equation

HRID 618986 reaction equation
[CH3:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([CH3:12])([CH2:5]3)[CH2:3]1)[CH2:9]2.[OH:13]N1C(=O)C2=CC=CC=C2C1=O.[C:25]([OH:28])(=O)[CH3:26]>>[CH3:12][C:4]12[CH2:10][CH:8]3[CH2:7][CH:6]([CH2:11][C:2]([CH3:1])([CH2:9]3)[CH2:3]1)[CH2:5]2.[OH:28][C:25]12[CH2:26][C:4]3([CH3:5])[CH2:10][CH:8]([CH2:9][C:2]([CH3:11])([CH2:3]3)[CH2:1]1)[CH2:7]2.[OH:28][C:25]12[CH2:26][C:6]3([CH3:7])[CH2:5][C:4]([CH3:12])([CH2:3][C:2]([OH:13])([CH2:11]3)[CH2:1]1)[CH2:10]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10665N-HydroxyphthalimideHCID 128001,3-Dimethyladamantane

Product 3

HCID 128001,3-DimethyladamantaneHCID 2657933,5-Dimethyl-1-adamantanolYield 39%HCID 5806055,7-Dimethyladamantane-1,3-diolYield 58%

Conditions

Temperature
70 °C

Procedure

A mixture of 1.64 grams (10 millimoles) of 1,3-dimethyladamantane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide, 0.015 gram (0.06 millimole) of Co(AA)2 and 10 milliliters of acetic acid was stirred under oxygen atmosphere at a temperature of 70° C. for six hours. As a result, with a transformation rate for 1,3-dimethyladamantane of 99%, 1-hydroxy-3,5-dimethyladamantane (yield 39%), and 1,3-dihydroxy-5,7-dimethyladamantane (yield 58%) were obtained. The selectivity for the alcohols was 97%.

Sources & evidence

ORD record
ord-2a851c4fea1843b5989ebbc860497b17
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Linked notes

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