반응 #1797475

반응 방정식

1-benzyloxy-6-tetradecanol

→

1,6-tetradecandiol

수율 9.7%

용매

methanol

반응 조건

실험 절차

The resulting compound, 1-benzyloxy-6-tetradecanol (16 g), was hydrogenated overnight using 100 mg of 10% palladium on activated carbon (Degussa A G; Frankfurt, Germany) in 100 ml of methanol to yield 1,6-tetradecandiol (11.1 g, 4.85 mmol). This diol compound, in 100 ml of methylene:pyridine (9:1), was treated with trityl chloride (13.5 g, 4.85 mmol). The mixture was stirred for 4 hours, then washed with ice-cold 10% HCl until the aqueous phase was acidic. Washing in brine then followed this until the aqueous phase was neutral. Solvent removal and chromatography on silica gel in hexane:ethylacetate (80:20) of the oil gave 20.1 g (87%) of the trityl alcohol. The chemical shift of the compound, detected by 1H-NMR, was as follows: 1H-NMR (CDCl3) δ 0.89 (t, 3H, CH3), 1.2-1.7 (m, 22H, CH2), 3.05 (m, 2H, CH2O), 3.55 (m, 1H, CH—O), 3.55 (m, 1H, CH—O), 7.2-7.5 (m, 15H, benzyl).

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