Acetic Acid → 3,5-Dihydroxyadamantane-1-carboxylic acid

HRID 1296386

Reaction equation

HRID 1296386 reaction equation
[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.[C]=O.O=O.[C:17]([OH:20])(=[O:19])C>>[C:17]([C:5]12[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)([OH:20])=[O:19]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 5738291,3-AdamantanediolHCID 178418416HCID 178418416, compound

Product 1

HCID 120106473,5-Dihydroxyadamantane-1-carboxylic acidYield 80%

Procedure

A reactor was charged with 10 mmole of 1,3-adamantanediol, 1 mmole of NHPI, 0.005 mmole of Co(AA)2 and 25 mL of acetic acid, then equipped with a gas bag of mixed gas (a mixed gas of 2 L of carbon monoxide and 0.5 L of oxygen; pressure: 5 kg/cm). The resultant mixture was stirred for 6 hours at 60° C. to give 1-carboxy-3,5-adamantanediol (yield 80%). The conversion of 1,3-adamantanediol was 99%.

Sources & evidence

ORD record
ord-f6c13d3b207045c4bada0a4f37f868fa
Source dataset
uspto-grants-2007_07
Patent number
USRE039744E1

Linked notes

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