1-(4-Benzyloxy-3-methoxyphenyl)ethanone

Pale Yellow Solid

A solution of 4-hydroxy-3- methoxyacetophenone (40 g, 240 mmol), benzyl bromide (31.4 ML, 260 mmol) and potassium carbonate (99.6 g, 360 mmol) in DMF (800 mL) was heated to 40 °C overnight. The solution was cooled to room temperature, poured over ice and the resultant solid was filtered. This material was washed with water and dried to give 1- (4-BENZYLOXY-3- methoxyphenyl) ethanone (61 g, 99 percent).A solution of 4-hydroxy-3- methoxyacetophenone (40 g, 240 mmol), benzyl bromide (31.4 mL, 260 mmol) and potassium carbonate (99.6 g, 360 mmol) in DMF (800 mL) was heated to 40 °C overnight. The solution was cooled to room temperature, poured over ice and the resultant solid was filtered. This material was washed with water and dried to give l-(4-benzyloxy-3- methoxyphenyl)ethanone (61 g, 99 percent).A solution of 4-hydroxy-3- methoxyacetophenone (40 g, 240 mmol), benzyl bromide (31.4 ML, 260 mmol) and potassium carbonate (99.6 g, 360 mmol) in DMF (800 mL) was heated to 40 °C overnight. The solution was cooled to room temperature, poured over ice and the resultant solid was filtered. This material was washed with water and dried to give 1- (4-BENZYLOXY-3- methoxyphenyl) ethanone (61 g, 99 percent).The mixture of 31.62 g (190 mmol) 1-(4-hydroxy-3-methoxy-phenyl)-ethanone, 16.36g (118mmol) potassium carbonate, 0.5g potassium iodide, 400ml acetone and 33.15 g (190 mmol) ml benzyl bromide were refluxed for 2 days. The solventULA-P03071WO21 Application was evaporated, the residue was taken up in 400 ml of water. The precipitate was filtered, washed with 100 ml of sodium carbonate saturated aqueous solution and 2 x100 ml of water, then dried on air to give 47.8 g of product [A]. Yield 98percent.Step 1) 1-(4-Benzyloxy-3-methoxyphenyl)ethanone6.7g (40 mmol) of D1 are successively 16.6g(120mmol) of potassium carbonate, 30ml DMF was added to a 100ml pear-shaped bottle, After stirring at 40 degrees Celsius for 10 minutes, 5.2 ml (44 mmol) of D2 was added and the reaction was carried out at 40 degrees Celsius for 4 hours. Cool to room temperature, add ice water to the reaction flask, filter, wash, After drying, white powdery solid product D3 12g (39.1 mmol) was obtained with a yield of 97.7percentA 100 mL dry flask was charged with acetovanillone (4.16 g, 0.025 mol) and anhydrous DMF (10 mL). Sodium hydride (1.05 g, 0.0263 mol, 60percent in mineral oil) was added and the reaction mixture was stirred at room temperature followed by the dropwise addition of benzyl bromide (3.1 mL, 0.0263 mol). The reaction was carried out at room temperature for 2 h, then poured into water. Ethyl acetate (150 mL) was used to extract out the compound and the organic layer was washed with water (2x100 mL), brine, dried over sodium sulfate, and concentrated to give the benzyl intermediate (6.21 g, 96percent), which was subsequently used without further purification.A 100 mL dry flask was charged with acetovanillone (4.16 g, 0.025 mol) and anhydrous DMF (10 mL). Sodium hydride (1.05 g, 0.0263 mol, 60percent in mineral oil) was added and the reaction mixture was stirred at it followed by the dropwise addition of benzyl bromide (3.1 mL, 0.0263 mol). The reaction was carried out at rt for 2 h, then poured into water. Ethyl acetate (150 mL) was used to extract out the compound and the organic layer was washed with water (2×100 mL), brine, dried over sodium sulfate, and concentrated to give the benzyl intermediate (6.21 g, 96percent), which was subsequently used without further purification.A mixture of 109 (100.0 g, 601.68 mmol), benzyl bromide (79.0 mL, 649.81 mmol) and potassium carbonate (249.0 g, 1.8 mol) in N, N-dimethylformamide (2000 mL) was heated to 40° C. overnight. The solution was cooled to room temperature, poured into ice water (1500 mL) and stirred for 1 h. The resultant solid was filtered and washed by H0.830 g (5 mmol) of acetovanillone (1), 1.026 g (6 mmol) of benzyl bromide, 0.828 g (6 mmol) of powdered potassium carbonate, and 10 mL of dimethyl formamide were added to a microwave accelerated reaction system (Milstone Ethos A, Italy). In a 500 ml flask Solanaceae, 4-hydroxy-3-methoxy aminoacetophenone of 20. 8g (125mmol, 1. 0eq. ), 220 ml monohydroxyacetone, potassium carbonate 17. 4g (126mmol, 1. 0eq. ) Put, 30 minutes after stirring at room temperature, a benzyl bromide 18 ml (151mmol, 1. 2eq. ) Addition, reflux in time at 60 °C 21. After condensing, the purified water and adding 200 ml, extracted with chloroform (100 ml × 3), magnesium sulfate waterlessly org. layer by drying, filtering, concentrated, recrystallization (ethyl acetate 50 ml, Phenylbicyclohexane 1 ml, 60 °C), suction filtration, vacuum drying, a first crystal is obtained. Concentrating somas, recrystallization (ethyl acetate 5 ml, 60 °C), suction filtration, vacuum drying, a second crystal is obtained. The white crystal (compd. (I1)), yielding: 29. 2g (114mmol, 91percent)is obtained.To a solution of acetovanillone (33) (4.70 g, 28.3 mmol) in MeCN (60 mL) was added KAt room temperature, 400.0 g (2.41 mol) of 3-methoxy-4-hydroxyacetophenone II was added to 2 L of DMF. 997.7 g (7.23 mol) of anhydrous potassium carbonate was added. After stirring for 15 min, a solution of 430.2 g (2.53 mol) of benzyl bromide was added dropwise. Drop finished. Stir at room temperature for 4 h. The reaction solution was poured into 10 L of ice water. Filter. Obtained 594.5 g of a white solid.Compound 18 (8.3 g, 50 mmol) was dissolved in DMF (50 mL) and then anhydrous K

Intermediate in the preparation of Epinephrine metabolites

Molecular Weight:256.30
XLogP3:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:256.109944368
Monoisotopic Mass:256.109944368
Topological Polar Surface Area:35.5
Heavy Atom Count:19
Complexity:284
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes