Acetic Acid → 1-Adamantanol

HRID 1978104Notes

Reaction equation

HRID 1978104 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[CH:5]12[CH2:14]C3C[CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2.ON1C(=O)C2=CC=CC=C2C1=O.O=O>>[C:1]12([OH:4])[CH2:2][CH:11]3[CH2:13][CH:7]([CH2:6][CH:5]([CH2:12]3)[CH2:14]1)[CH2:8]2

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 9238Adamantane2×HCID 10665N-Hydroxyphthalimide

Product 1

HCID 641521-AdamantanolYield 37%

Procedure

To 25 mmol of acetic acid were added 10 mmol of adamantane, 1 mmol of N-hydroxyphthalimide (NHPI) and a binary co-catalyst [0.03 mmol of acetylacetonatovanadium V(AA)3 and 0.02 mmol of actylacetonatomangan Mn(AA)3], and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 75° C. for 6 hours. The products in the reaction mixture were analyzed by gas chromatography, and, as a result, the adamantane was converted into 1-adamantanol (yield: 37%). 1,3-adamantanediol (yield: 35%). 1,3,5-adamantanetriol (yield: 5%), 1,3,5,7-adamantane-tetranol (yield: 4%) with the adamantane conversion of 100%. The spectrum data of the 1,3,5,7-adamantanetetranol was as follows:

Sources & evidence

ORD record
ord-d87dc56aa20b437cb588e70544a30dc1
Source dataset
uspto-grants-2001_05
Patent number
US06235851B1

Reaction notes

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