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With potassium carbonate; In acetone; for 16.0h;Heating / reflux;
Preparation of 4-benzyloxy-3-methoxy-methylbenzoate 2.84 g of 4-benzyloxy-3-methoxy-benzoic acid was combined with 3.04 g of potassium carbonate and 1.03 mL of iodomethane in 100 mL of acetone. The mixture was refluxed for 16 hours, cooled to room temperature and diluted with dichloromethane. The slurry was filtered and washed with dichloromethane and the filtrate concentrated to dryness. The solids were redissolved in dichloromethane, washed twice with water, dried over sodium sulfate and filtered. The filtrate was concentrated to a clear, colorless oil which was triturated with methanol to give a white solid in 90% yield (2.7 grams). Proton
With sodium hydroxide; In methanol; for 4.0h;Heating / reflux;
E) 4-Benzyloxy-3-methoxy benzoic acid; A solution of sodium hydroxide (2.0 g) in methanol (50 ml) was added to a solution of 4-benzyloxy-3-methoxy benzoic acid methyl ester (4.64 g) in methanol (50 ml) and refluxed for 4 hrs. After removal of methanol under reduced pressure the residue was dissolved in water (150 ml) and washed with ethyl acetate (2 x 50 ml). The aqueous layer was acidified with 2N hydrochloric acid to pH 2. The precipitated product was collected by filtration which on drying under vacuum provided 4.17 g of 4-benzyloxy- 3-methoxy benzoic acid. (Yield = 74%) 'H NMR CDCl3 7.7 (1H, d, J = 8Hz) 7.63 (1H, s) 7.3-7.5 (5H, m) 6.92 (1H, d, J 8Hz) 5.25 (2H, s) 3.98 (3H, s)
(1) Benzyl bromide (3.59 ml) and potassium carbonate (5.69 g) were added to an acetone (50 ml) solution of methyl 4-hydroxy-3-methoxybenzoate (5.00 g), and heated at reflux for 4 hours. After removing solid matter by filtration and concentrating the filtrate under reduced pressure, the residue was dissolved in ethyl acetate, and washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure, thereby giving 7.47 g of <strong>[56441-97-5]methyl 4-benzyloxy-3-methoxybenzoate</strong>.(2) An aqueous 2 M sodium hydroxide solution (13.72 ml) was added to an ethanol (15 ml) solution of the above-obtained 4-benzyloxy compound (7.47 g), and heated at reflux for 2 hours. After evaporating the solvent under reduced pressure, 2M hydrochloric acid was added, and the thus-precipitated crystals were filtered, thereby giving 7.00 g of the desired compound.
With sulfuric acid; In methanol; for 10.0h;Reflux;
A catalytic amount of concentrated H2SO4 was added to a solution of compound 3 (5.4g, 20.9mmol) in 50mL of methanol and the mixture was refluxed for 10h. It was allowed to cool. The product crystallization from solution gave pure 4 (4.5g) as a white solid with a yield of 80%. Mp: 70-72C; 1H NMR (CDCl3, 300MHz): delta (ppm) 3.90 (s, 3H), 3.95 (s, 1H), 5.23 (s, 2H), 7.32-7.57 (m, 5H), 7.58 (s, 1H), 7.60-7.61 (d, J=2.0Hz, 1H), 7.63-7.64 (d, J=1.8Hz, 1H).
With sulfuric acid; In methanol; for 10.0h;Reflux;
A solution of 3-methoxy-4-benzyloxybenzoic acid (20.9 mmol, 5.4 g) in 50 ml of methanol was added to a 250 ml reaction flask, and 1 ml of concentrated sulfuric acid was slowly added dropwise with stirring. The mixture was heated under reflux for 10 hours.Concentrated and crystallized from methanol, filtration, the filter cake washed with a small amount of methanol, and dried to give a white solid 4.5g, 3-methoxy-4-benzyloxy-benzoic acid methyl ester Yield% 80,
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