Sodium Chloride → 1,4-Bis(4-methoxybenzyloxy)butan-2-ol

Participants

Reaction Steps

To a solution of mercury (II) trifluoroacetate (17.1 g, 40 ml) in aqueous tetrahydrofuran (1:1, 80 ml) was added a solution of 1,4-bis(4-methoxybenzyloxy)but-2-ene (12.8 g, 39 mmol) in tetrahydrofuran (10 ml) over 5 minutes. The resulting 2-phase mixture was stirred vigorously at room temperature for 15 minutes. To the mixture was added aqueous sodium hydroxide (40 ml, 3M) followed by sodium borohydride (0.5M solution in 3M sodium hydroxide; 40 ml) with water-bath cooling. The solution was saturated with sodium chloride and allowed to stand. The organic layer was collected, dried (magnesium sulphate) and filtered through celite. The solvent was removed to afford 1,4-bis(4-methoxybenzyloxy)butan-2-ol (12.27 g, 91%), IR: υmax (KBr) 3440, 2940, 2860, 1610, 1510 and 1250 cm-1 ; 1H NMR: δH (CDCl3) 1.76 (2H, q, J=6.0 Hz, 3-H), 2.90 (1H, br, D2O exchangeable, OH), 3.41 (2H, AB of ABX JAX =6.9 Hz, JBX =4.2 Hz and JAB =9.5 Hz, 1-H), 3.62 (2H, m, 4-H), 3.80 (6H, s, 2×CH3), 4.00 (1H, m, 2-H), 4.43 (2H, s, ArCH2), 4.48 (2H, s, ArCH2), 6.86 (4H, m, ArH) and 7.24 (4H, m, ArH).

Provenance & Evidence