2-Chloroethanol → (2-Chloroethoxy)-adamantylideneadamantane

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The bromo-substituted compound having formula 16 (220 mg, 0.58 mmol) was dissolved in dry dioxane (10 cm3) and 2-chloroethanol (5 cm3) was added. The mixture was refluxed for 18 hours, cooled, and concentrated at a reduced pressure. Water (50 cm3) was added and the product was twice extracted with n-hexane, with the combined extracts being washed with brine. The hexane solution was dried with MgSO4, filtered and concentrated at a reduced pressure. Columnchromatography over Al2O3 (act. II/III), using hexane as the eluent, produced 180 mg (0.52 mmol, 89.7%) of pure compound having formula 23 in the form of a colourless oil. IR (neat) 2950 (s), 1455 (m), 1100 (s) and 785 cm-1 (s) 1H-NMR (CCl4, TMS): δ 3.6 (double triplet, 4H), 3.25 (m, 1H), 2.85 (m, 5H), δ 2.4-1.1 (m, 22H), 13C-NMR (CBCl3): δ 135.8; 130.8; 82.6 (d); 67.9 (t); 43.2 (t); 39.7; 39.6; 39.5; 39.1; 37.1; 36.8; 35.7; 33.0; 32.4; 32.1; 31.8; 31.0; 30.1; 28.4 and 27.6. Mass: M+ at m/e 346 (100%). Exact mass: calculated for C22H31ClO: 346.206. Found 346.205.

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