| 94% |
|
4.13 Benzyl 2-hydroxybenzoate 25 NaHCO3 (1.46?g, 17.4?mmol, 1.2 equiv.) was added to a solution salicylic acid 1 (2?g, 14.5?mmol, 1 equiv.) in DMF (20?mL) and the resulting mixture was stirred at 70?C for 10?min. The temperature was reduced to 50?C followed by the addition of benzylbromide (1.81?mL, 15.2?mmol, 1.05 equiv.). The reaction mixture was stirred for 4?h and then allowed to cool to RT. H2O (50?mL) was added and the crude product was extracted with EtOAc (4?*?60?mL). The combined EtOAc extracts were washed with brine (50?mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. Purification of the crude residue by silica gel chromatography (Hexane/EtOAc, 5:0.2) afforded compound 25 as clear oil (3.11?g, 94%). HPLC purity (>99%). 1H NMR (CDCl3, 400?MHz): delta?=?5.42 (s, 2?H, CH2), 6.9 (m, 1?H, Ar-H), 7.4 (m, 6?H, Ar-H), 7.91 (q, 1?H, Ar-H), 10.78 (s, 1?H, O-H). 13C NMR (CDCl3, 100?MHz): delta?=?67.0 (CH2), 112.4 (Ar-C), 117.6 (Ar-C), 119.2 (Ar-C), 128.3 (Ar-C), 128.6 (Ar-C), 128.7 (Ar-C), 130.0 (Ar-C), 135.3 (Ar-C), 135.8 (Ar-C), 161.8 (Ar-C), 170.0 (C=O). ATR-FTIR: upsilonmax?=?3188 (m, br, O-H), 3000 (m, Ar C-H), 1670 (s, C=O), 1086 and 1133 (s, C-O) cm-1. |
| 76% |
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 16h; |
BnBr (1.75 mL, 14.631 mmol) was added to a solution of salicylic acid (2.0 g, 14.625 mmol) in TBAF (17.5 mL, 1 M solution in THF) and the reaction mixture was stirred at r.t. overnight (16 h). The organic layer was poured into H2O (100 mL) and extracted with EtOAc (70 mL). It was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (2% EtOAc/hexanes) to furnish 2.53 g of benzyl 2-hydroxybenzoate (colourless oil, yield: 76%).1H NMR (CDCl3, 250 MHz) delta ppm: 10.75 (s, 1H), 7.87 (t, J=7.1 Hz, 1H), 7.42 (m, 6H), 6.97 (t, J=7.4 Hz, 1H), 6.86 (c, J=7.1 Hz, 1H), 5.38 (s, 2H). |
| 76% |
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 16h; |
Step 1 : Benzyl 2-hydroxybenzoate BnBr (1.75 mL, 14.63 1 mmol) was added to a solution of salicylic acid (2.0 g, 14.625 mmol) in TBAF (17.5 mL, 1 M solution in THF) and the reaction mixture was stirred at r.t. overnight (16 h). The organic layer was poured into H20 (100 mL) and extracted with EtOAc (70 mL). It was dried over Na2S04 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on Si02 (2% EtOAc/hexanes) to furnish 2.53 g of benzyl 2- hydroxyb enzo ate (colourless oil, yield: 76%). NMR (CDCI3, 250 MHz) delta ppm: 10.75 (s, 1H), 7.87 (t, J = 1.1 Hz, 1H), 7.42 (m, 6H), 6.97 (t, J = 7.4 Hz, 1H), 6.86 (c, J = 7.1 Hz, 1H), 5.38 (s, 2H). |
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