Synthesis
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 ?C (Lit.: 186 – 188 ?C)109;
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]-).
