Oxygen → HCID 22670571, compound

HRID 1181659Notes

Reaction equation

C12([OH:11])CC3CC(CC(C3)C1)C2.ON1C(=O)C2=CC=CC=C2C1=O.O=O.[C:26]12([OH:37])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH:27]1[OH:36])[CH2:33]2>ClC1C=CC=CC=1.C(O)(=O)C>[C:26]12([OH:37])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[C:27]1([OH:11])[OH:36])[CH2:33]2

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 25 g (164 mmol) of adamantanol, 5.36 g (32.8 mmol) of N-hydroxyphthalimide, 0.11 g (0.328 mmol) of vanadiumacetylacetonato [V(acac)3], 150 mL of acetic acid and 150 mL of chlorobenzene was stirred for 20 hours at 85° C. and 1 atm (0.101 MPa) in an atmosphere of oxygen. After completion of reaction, the reaction mixture was analyzed by gas chromatography and high performance liquid chromatography, and, as a result, the conversion of adamantanol was 95.6%, adamantanediol and adamantanetriol were formed in yield 50.5% (selectivity 52.8%) and yield 40.7% (selectivity 42.6%), respectively. Moreover, in the reaction mixture, 1.85 g of N-hydroxyphthalimide used as a catalyst, 1.51 g of phthalimide, and 0.40 g of phthalic anhydride were contained.

Workup

customAfter completion of reaction

Sources & evidence

ORD record: ord-5de233dc5e654e5fa1a6f350b9134d48
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285684B2

Reaction notes

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