ChemicalBook CAS DataBase List 5-Hydroxyadamantan-2-one

5-Hydroxyadamantan-2-one synthesis

7synthesis methods

Product Name:5-Hydroxyadamantan-2-one
CAS Number:20098-14-0
Molecular formula:C10H14O2
Molecular Weight:166.22

700-58-3 Synthesis

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

20098-14-0
274 suppliers
$5.00/100mg

Yield:20098-14-0 74%

Reaction Conditions:

Stage #1:2-Adamantanone with nitric acid at 60; for 74.25 h;Cooling with ice;
Stage #2: with sulfuric acid;water for 1 h;Heating;

Steps:

3.i
Step (i): Preparation of compound of formula (11)Adamantanone (50 grams, 333 mmol) was added with stirring to nitric acid (98%, 440 mL) at ice bath temperature over a period of 15 minutes. The reaction mixture was stirred at room temperature for 72 hours and then heated at 60 °C, for 2 hours until most of the nitrogen dioxide evaporated. Excess nitric acid was distilled off under reduced pressure. The light yellow oil solidified upon cooling. The reaction mixture was diluted with water (200 mL) and concentrated sulphuric acid (75 mL). The resultant clear yellow solution was heated on the steam bath in a hood for 1 hour. The reaction mixture was neutralized with 30% aqueous sodiumhydroxide solution, and while warm, extracted with chloroform. The extracts were combined, washed with brine solution and concentrated in vacuum. The crude product was dissolved in dichloromethane ( 15 mL) and hexane was added until no more precipitate was formed. The solid material was isolated by filtration and dried under vacuum to obtain compound of formula (11) (40.9 grams). Yield: 74 %. Melting Range: 278.8-300 °C; -NMR (CDCI3): δ 2.69 (bs, 2H), 2.36-2.32 (m, 2H), 2.12-2.02 (m, 2H), 2.02-1 :88 (m, 6H), 1.80- 1.68 (m, 1H).IR: 3410, 2929, 2855, 2645, 1725, 1539, 1452, 1351, 1288, 1 1 16, 1055, 927, 900, 797;Mass (m/z): 167 [Μ+Η⁺].

References:

SUVEN LIFE SCIENCES LIMITED;NIROGI, Ramakrishna;MOHAMMED, Abdul, Rasheed;AHMAD, Ishtiyaque;JAYARAJAN, Pradeep;KANDIKERE, Nagaraj, Vishwottam;SHINDE, Anil, Karbhari;KAMBHAMPATI, Rama, Sastri;BHYRAPUNENI, Gopinadh;RAVULA, Jyothsna;PATNALA, Sriramachandra, Murthy;JASTI, Venkateswarlu WO2011/30349, 2011, A1 Location in patent:Page/Page column 23-24

FullText