1,3-Adamantanediol

white crystal

The procedure of was repeated, except that the catalyst was replaced by a catalyst that vanadium (18 μmol) is supported on montmorillonite (i.e., a V/Mont. catalyst); the amount of adamantane employed was changed to 3 mmol; t-butyl acetate was employed as a solvent; and reaction was performed at 100° C. for 96 hours. The V/Mont. catalyst was formed through the catalyst preparation process described in Japanese Patent Application Laid-Open (kokai) No. 2004-2234. Specifically, the catalyst was obtained by adding an aqueous vanadium(III) chloride solution to montmorillonite (Kunipia F, product of Kunimine Industries Co., Ltd.), followed by ion exchange, filtration, washing with water, drying, and firing in air at 800° C.A mixture of 25 g (0.164 mol) of 1-adamantanol I, 2.68 g (0.0164 mol) of NHPI, 0.482 g (1.64 mmol) of Co(acac)2, 0.715 g (0.0082 mol) of MnO2, and 250 mL of glacial acetic acid was heated under vigorous stirring to 60°C and then stirred at that temperature upon stirring and bubbling with oxygen during 30 h. After cooling, acetic acid was removed. The residue was dissolved in 250 mL of chloroform and heated at reflux during 2 h. Solid adamantane-1, 3, 5-triol III was filtered off and recrystallized from ethyl acetate. Yield 15.7 g (52 percent), mp 202–204°C (mp 203–205°C [17]). Adamantane-1, 3-diol II precipitated from chloroform was filtered off and dried. Yield 10.7 g (39 percent), mp 296–297°C (mp 298–300°C [26]). Mass spectrum, m/z (Irel, percent): 1, 152 (35) [M]+, 109 (10), 95(100); II, 168 (28) [M]+, 150 (4), 111 (100), 95 (14);III, 184 (10) [M]+, 166 (6), 150 (50), 127 (100), 111(46), 92 (28).The procedure of was repeated, except that the catalyst was replaced by NHPI (1 mmol) and VO(acac)The procedure of Example 6 was repeated, except that the amount of the catalyst was changed to 10 μmol, and the adamantane was replaced by 1-adamantanol (5 mmol).The procedure of was repeated, except that the acetic acid serving as a solvent was replaced by propionic acid.The procedure of was repeated, except that methanesulfonic acid [CHThe procedure of was repeated, except that europium triflate [Eu(OTf)The procedure of Example 6 was repeated, except that the amount of adamantane employed was changed to 5 mmol, and the catalyst was replaced by Co(acac)The procedure of was repeated, except that the catalyst was replaced by a vanadium oxide-TPP complex [VOTPP].The procedure of Example 6 was repeated, except that the amount of adamantane employed was changed to 5 mmol, and the reaction temperature was changed to 100° C.Firstly, to a solution of adamantane (2.59g, 19mmol) in a mixture of acetic acid (100mL) and concentrated sulphuric acid (0.52mL 9.5mmol) was slowly added chromium trioxide (7.6g, 76mmol). The resultant reaction system was stirred at 80°C for 2h. Then the mixture was concentrated, washed with 30percent NaOH solution, and extracted with ethyl acetate. The organic extract was cooled down at room temperature overnight to give a white precipitate which was recrystallized from a mixed solvent of ethanol and hexane to afford white solid 1. General procedure: Adamantane carboxylic acid 1a–1s or 3, 0.5 g, wasadded in portions under vigorous stirring and cooling to a mixture of 2.5, 3, or 7 equiv of MnO2 and 2.5–14 mL of 93percent H2SO4, maintaining the temperature within 25-30°C. The mixture was kept for 0.5–24 h at that temperature and treated with cold water on coolingwith an ice bath. The precipitate was filtered off andwashed with a small amount of water and butan-1-ol. The products were extracted with butan-1-ol (5 ×2 mL). In the isolation of 2j–2l and 2q–2s, the mixture was adjusted to pH 3–4 with 30percent aqueous sodium hydroxide prior to extraction. The organic phases werecombined, washed with water, a solution of sodiumhydrogen carbonate, and water again, and dried byazeotropic distillation. The solvent was removed under reduced pressure on a rotary evaporator, and the product was purified by recrystallization.The procedure of was repeated, except that the catalyst was replaced by acetylacetonatovanadium [V(acac)Adamantane (10 mmol, 1.36 g) and acetylacetonatovanadyl [VO(acac)The procedure of was repeated, except that the catalyst was replaced by ammonium metavanadate [NH

1,3-adamantanediol is an important synthetic intermediate used in the field of IT technology. Used as medicine and pesticide intermediates.

Molecular Weight:168.23
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:168.115029749
Monoisotopic Mass:168.115029749
Topological Polar Surface Area:40.5
Heavy Atom Count:12
Complexity:190
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes