Hydrochloric Acid → HCID 53258695, compound

Participants

Reaction Steps

3,4,5-Tris(octadecyloxy)benzyl alcohol (83.0 g, 90.8 mmol) was dissolved in chloroform (830 ml), thionyl chloride (21.6 g, 0.182 mol) was added at 0° C., and the mixture was stirred at room temperature for 1.5 hr. The solvent was evaporated, and the residue was precipitated with acetonitrile (800 ml) to give 3,4,5-tri(octadecyloxy)benzylchloride (93.6 g) as wet crystals. (ii) 3,4,5-Tri(octadecyloxy)benzylchloride (93.6 g, wet, <90.8 mmol), 2-hydroxy-4-methoxybenzaldehyde (15.2 g, 0.10 mol) and potassium carbonate (31.4 g, 0.23 mol) were suspended in DMF (830 ml), and the suspension was stirred at 80° C. overnight. The reaction mixture was dissolved in chloroform (1600 ml), and the mixture was washed 3 times with 1N hydrochloric acid (800 ml), once with 5% aqueous sodium hydrogen carbonate solution (800 ml), and once with 20% brine (800 ml). The solvent was evaporated, and the residue was precipitated with methanol (800 ml) and washed with acetonitrile (800 ml) to give 4-methoxy-2-[3′,4′,5′-tris(octadecyloxy)benzyloxy]benzaldehyde (93.5 g, 89.2 mmol, 98%). (iii) 4-Methoxy-2-[3′,4′,5′-tris(octadecyloxy)benzyloxy]benzaldehyde (93.5 g, 89.2 mmol) was dissolved in THF-methanol (1870 ml+94 ml), and sodium borohydride (4.05 g, 107 mmol) was added at 0° C. After stirring at room temperature for 1.5 hr, 0.2N hydrochloric acid (100 ml) was added at 0° C. to quench the reaction. The solvent was evaporated to about half, and dissolved in chloroform (2400 ml). The mixture was washed twice with 0.1N hydrochloric acid (1200 ml), once with 5% aqueous sodium hydrogen carbonate solution (1200 ml), and once with 20% brine (1200 ml). The solvent was evaporated, and the residue was precipitated with methanol (900 ml) and washed with acetonitrile to give 4-methoxy-2-[3′,4′,5′-tris(octadecyloxy)benzyloxy]benzyl alcohol (92.4 g, 88.0 mmol, 97% yield vs 3,4,5-tris(octadecyloxy)benzyl alcohol).

Provenance & Evidence