Sodium Hydroxide → 9-(1,3-Benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylic acid

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Reaction Steps

A solution of 4 (56 mg, 0.11 mmol) and NaOH (16 mg, 0.4 mmol) in MeOH/H2O (4:1, 2 mL) was heated at 70° C. for 12 h. The solvent was evaporated to dryness, and the residue was dissolved in water. The aqueous solution was acidified to pH 1-2 with 10% aqueous HCl solution and then extracted with ether (3×50 mL). The extract was washed with water and brine, and dried over MgSO4. The evaporation of solvent yielded 5 (32 mg, 70%) as a white powder. mp 219-221° C.; 1H NMR (DMSO-d6) δ 8.27 (s, 1H, H4), 7.70 (d, 1H, H5, J=8.7 Hz), 7.38 (d, 1H, H6, J=8.7 Hz), 7.17-7.25 (m, 5H, OCH2Ph), 6.89 (d, 1H, H5′, J=8.1 Hz), 6.79 (d, 1H, H2′, J=1.5 Hz), 6.65 (dd, 1H, H6′, J=1.5, 8.1 Hz), 6.06 (AB, 2H, 3′,4′-OCH2O—, Δδ=18.0 Hz, J=0.6 Hz), 5.85 (AB, 2H, 7,8-OCH2O—, Δδ=9.3 Hz, J=0.9 Hz), 4.53 (s, 2H, 2-CH2OCH2Ph), 4.24 (s, 2H, 2-CH2OBn); MS (FAB, positive) m/z 457 [M+H]+.

Provenance & Evidence