反应详情

温度

0 °C

3-Acetoxy-4-pentyloxy-benzaldehyde (0.75 g., 3.0 mmol, 1 equiv.) is dissolved in 15 mL of MeOH, and the mixture cooled to 0° C. Sodium borohydride (0.230 g., 6 mmol., 2 equiv.) is added in portions. After stirring for 30 min., the mixture is neutralized with 1N HCl, and then extracted thrice with ether. The extracts are washed with brine, dried (MgSO4), and evaporated. Chromatography on silica gel using CH2Cl2 /hexane affords 3-acetoxy-4-pentyloxy-benzyl alcohol (12f) (0.680 g., 2.70 mmol., 90%): mp=35°-36° C.; 1H NMR (300 MHz, CDCl3) δ 7.17 (dd, J=2, 8 Hz, 1H, ArH), 7.05 (d, J=2 Hz, 1H, ArH), 6.92 (d, J=8 Hz, 1H, ArH), 4.85 (s, 1H, OH), 4.60 (s, 2H, ArCH2O), 3.95 (t, J=7 Hz, 2H, OCH2R), 2.30 (s, 3H, CH3CO), 1.75 (m, 2H, OCH2CH2), 1.38 (m, 4H, CH2CH2CH3), 0.90 (t, J=7 Hz, 3H, RCH2CH3).

1. extractionextracted thrice with ether
2. washThe extracts are washed with brine
3. dry with materialdried (MgSO4)
4. customevaporated