Acetic Acid → 1-Adamantanol

HRID 1978105Notes

Reaction equation

HRID 1978105 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[O:11]=O.[C:13]([OH:16])(=[O:15])[CH3:14]>>[C:1]12([OH:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:13]12([OH:16])[CH2:14][CH:7]3[CH2:6][CH:5]([CH2:10][C:1]([OH:11])([CH2:8]3)[CH2:2]1)[CH2:4]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 977OxygenHCID 9238Adamantane3×

Product 2

HCID 641521-AdamantanolYield 48%HCID 5738291,3-AdamantanediolYield 13%

Procedure

To 25 ml of acetic acid were added 10 mmol of adamantane, 0.8 mmol of NHPI and 0.6 mmol of acetylacetonatocobalt(II)Co(AA)2 , and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 75° C. for 3 hours. The products in the reaction mixture were analyzed by gas chromatography, and, as a result, adamantane was converted into 1-adamantanol (yield: 48%) and 1,3-adamantanediol(yield: 13%) with the adamantane conversion of 65%.

Sources & evidence

ORD record
ord-8fb1a8c44d00424c9ad67f50a6e6df6f
Source dataset
uspto-grants-2001_05
Patent number
US06235851B1

Reaction notes

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