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

20098-14-0

Step (i): Synthesis of 5-hydroxy-2-adamantanone (compound of formula 11) Under cooling in an ice bath, adamantanone (50 g, 333 mmol) was slowly added to concentrated nitric acid (98%, 440 mL) for 15 min while stirring was maintained. The reaction mixture was stirred continuously for 72 h at room temperature and then warmed to 60 °C for 2 h until most of the nitrogen dioxide gas escaped. Excess nitric acid was removed by distillation under reduced pressure and the resulting pale yellow oil solidified on cooling. The reaction mixture was sequentially diluted with deionized water (200 mL) and concentrated sulfuric acid (75 mL), and the resulting clarified yellow solution was heated on a steam bath in a fume hood for 1 hour. The reaction solution was neutralized with 30% aqueous sodium hydroxide under warm conditions and subsequently extracted with chloroform. The organic phases were combined, washed with saturated saline and concentrated under reduced pressure. The crude product was dissolved in dichloromethane (15 mL), hexane was added dropwise until the precipitate was no longer generated, the solid was collected by filtration and dried under vacuum to give 5-hydroxy-2-adamantanone (compound of formula 11, 40.9 g) in 74% yield. Characterization data: Melting point: 278.8-300°C; 1H-NMR (CDCl3) 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 (cm-1): 3410, 2929, 2855, 2645, 1725, 1539, 1452, 1351, 1288, 1116, 1055, 927, 900, 797; Mass spectrum (m/z): 167 [M+H]+.

700-58-3 Synthesis

700-58-3
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20098-14-0
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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

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