1-Adamantanol

Description

1-Adamantanol is a cyclic molecule with a hydroxyl group. It is produced by the oxidation of 2-methyl-2-adamantanol. 1-Adamantanol has been shown to be an effective substrate for bioremediation in wastewater treatment plants and can be used as a precursor to produce trifluoroacetic acid.

Chemical properties

white to off-white crystalline powder or needles

The Uses of 1-Adamantanol

1-Adamantanol was used in the preparation of 1,3-adamantanediol. It is used in the manufacture of synthetic adamantane derivatives and adapalene.

Synthesis Reference(s)

Synthetic Communications, 19, p. 2061, 1989 DOI: 10.1080/00397918908052598
Tetrahedron Letters, 28, p. 1941, 1987 DOI: 10.1016/S0040-4039(00)96015-5

Purification Methods

If 2-adamantanol is a suspected impurity, then dissolve the substance (10g) in acetone (100mL) and add Jones's reagent [CrO3 (10.3g) in H2O (30mL)], then conc H2SO4 (8.7mL) is added dropwise (turns green in colour) until excess reagent is present (slight red colour). Stir overnight, decant the acetone solution from the Cr salts and adamantan-2-one, dry (Na2SO4) and evaporate to dryness. The residue (ca 7g) is chromatographed through Al2O3 (250g) and washed with 50% *benzene/pet ether (b 40-60o), then 100% Et2O (to remove any adamantan-2-one present) and the 1-adamantanol is then eluted with 5% MeOH in Et2O. The eluate is evaporated, and the residue is recrystallised from pet ether (b 30-60o) at -70o, m 287.2-288.5o. It also crystallises from MeOH and can be sublimed in vacuo. It has characteristic IR, max 3640, 1114, 1086, 982 and 930cm-1. [Schleyer & Nicholas J Am Chem Soc 83 182 1961.] [Beilstein 6 IV 391.] Alternatively, if free from the 2-isomer, dissolve it in tetrahydrofuran, dilute with H2O to precipitate the alcohol. Collect, dry and sublime it in a vacuum at 130o. [Stetter et al. Chem Ber 92 1629 1959.]