ChemicalBook CAS DataBase List 2-Adamantanone

2-Adamantanone synthesis

8synthesis methods

Product Name:2-Adamantanone
CAS Number:700-58-3
Molecular formula:C10H14O
Molecular Weight:150.22

281-23-2
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$5.00/25g

700-58-3
450 suppliers
$5.00/5g

768-95-6 Synthesis

768-95-6
432 suppliers
$10.00/5g

Yield:700-58-3 70%

Reaction Conditions:

with pyridine;bis(acetylacetonate)oxovanadium;dihydrogen peroxide;Hexafluoroacetone in water at 60;Catalytic behavior;Temperature;Reagent/catalyst;

Steps:

Adamantan-2-one (4).

A reaction flask was charged with 1 mmol of adamantane (1), 0.14 mmol of VO(acac)2, 25 mmol of acetic acid, and 35 mmol of pyridine. The solution was heated to 60°C, and a mixture of 10 mmol of 32% hydrogen peroxide and 0.5 mmol of hexafluoroacetone sesquihydrate was added dropwise from a dropping funnel over a period of 5 h. The mixture was cooled to 20°C, washed with brine, and extracted with ethyl acetate (3 × 5 mL). The extract was evaporated under reduced pressure, and the residue was subjected to chromatography on silica gel using hexane-ethyl acetate (first 9 : 1 and then 7 : 3) as eluent. Yield 70%, mp 256-257°C (sublimes); published data [8]: mp 256-258°C. 13C NMR spectrum, δC, ppm: 27.64 (C5, C7), 36.31 (C6), 39.20 (C4, C8, C9, C10), 46.92 (C1, C3), 216.59 (C2). Found, %: C 79.78; H 9.12. C10H14O. Calculated, %: C 79.95; H 9.39.

References:

Kislitsina;Shchadneva;Khusnutdinov [Russian Journal of Organic Chemistry,2018,vol. 54,# 7,p. 992 - 995][Zh. Org. Khim.,2018,vol. 54,# 7,p. 990 - 993,4]

700-57-2 Synthesis