3-(Hydroxymethyl)naphthalen-2-ol

Synthesis

3-(hydroxymethyl)naphthalen-2-ol is prepared by reacting;Methyl 3-hydroxy-2-naphthoate with;sodium borohydride in;methanol.Methyl 3-hydroxy-2-naphthoate (100 mg, 0.49 mmol) was dissolved in methanol (7.0 ml) with stirring in a round bottom flask. Sodium borohydride (185 mg, 4.90 mmol) was then added in carefully into the reaction mixture in two portions with an interval time of 3 hours between them and left to react overnight. The resultant mixture was quenched with addition of water followed by extraction with ethyl acetate (3×10 ml). The organic extracts were collected, dried with magnesium sulphate and concentrated in vacuo to give the colourless powder title compound as a colourless powder (82 mg, 96%): mp: 193 – 195 ℃ (Lit.: 186 – 188 ℃);
vmax/cm-1 3379 br. m (O-H), 2844 w (aro. C-H), 1500 s (aro. C=C); δH (300 MHz; DMSO-d6) 9.82 (1H, br. s., OH), 7.80 (1H, s, C(1)H), 7.76 (1H, d, J 8.1, C(5)H or C(8)H), 7.64 (1H, d, J 8.1, C(5)H or C(8)H), 7.33 (1H, ~t, J 7.5, C(6)H or C(7)H), 7.23 (1H, ~t, J 7.5, C(6)H or C(7)H), 7.09 (1H, s, C(4)H), 5.17 (1H, br. s., OH), 4.63 (2H, br. s., C(9)H2); δC (75 MHz; DMSO-d6) 153.1 (Ar-C), 133.3 (Ar-C), 131.8 (Ar-C) 127.7 (Ar-C), 127.3 (Ar-CH), 125.5 (Ar-CH), 125.4 (Ar-CH), 125.3 (Ar-CH), 122.6 (Ar-CH), 107.9 (Ar-CH), 58.6 (C(9)H2); m/z (-ES) 173 (100%, [MH]-), 174 (12%, [M]-).