Acetic Acid → 1,3,5,7-Tetrahydroxyadamantane

HRID 618988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 618988
[C:1]12([OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:13]N1C(=O)C2=CC=CC=C2C1=O.[C:25]([OH:28])(=O)[CH3:26]>>[C:5]12([OH:13])[CH2:10][C:1]3([OH:12])[CH2:8][CH:7]([CH2:9][C:3]([OH:11])([CH2:2]3)[CH2:4]1)[CH2:6]2.[C:25]12([OH:28])[CH2:26][C:7]3([OH:13])[CH2:8][C:1]([OH:12])([CH2:2][C:3]([OH:11])([CH2:9]3)[CH2:4]1)[CH2:10]2

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 10665N-HydroxyphthalimideHCID 5738291,3-Adamantanediol2×

Produkt 2

HCID 8200931,3,5,7-TetrahydroxyadamantaneAusbeute 62 %HCID 98990221,3,5-AdamantanetriolAusbeute 37 %

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 1.68 grams (10 millimoles) of 1,3-adamantanediol, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide, 0.015 gram (0.06 millimole) of Co(AA)2 and 25 milliliters of acetic acid was stirred under an oxygen atmosphere at a temperature of 95° C. for 6 hours. Thus, 1,3-adamantanediol was transformed, with a transformation rate of 99%, into 1,3,5-adamantanetriol (selectivity for 1,3-adamantanediol 37%, yield 37%) and 1,3,5,7-adamantanetetraol (selectivity for 1,3-adamantanediol 62%, yield 62%). The selectivity for the alcohols was 99%.

Quellen und Nachweise

ORD-Eintrag
ord-712bd5ea89924bcdae091b67af9d7139
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958821

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