4-ethoxy-3-hydroxybenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.6 grams of 4-ethoxy-3-hydroxybenzaldehyde (100 mmol.) and 200 ml of absolute ethyl alcohol are added to a three-necked flask and then heated to 40° C. for being dissolved, 9 grams of potassium carbonate (65.07 mmol.) is added, 15 ml of benzyl chloride (130.13 mmol.) is added under stirring, heating reflux is performed for 1 hour, the reaction product is cooled to 50° C. after complete reaction is detected by TLC and then filtered while it is hot, the filtrate is put in a refrigerator for being cooled over night, crystals are separated out and pump-filtered, filter cakes are washed with 30 mL of absolute ethyl alcohol and then vacuum-dried to obtain 21.5 grams of white needle crystals, and the yield is 83.9%. for being dissolved heating reflux the reaction product is cooled to 50° C. after complete reaction filtered while it for being cooled over night crystals are separated out pump-filtered filter cakes are washed with 30 mL of absolute ethyl alcohol vacuum-dried

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.6 grams of 4-ethoxy-3-hydroxybenzaldehyde (100 mmol.) and 200 ml of absolute ethyl alcohol are added to a three-necked flask and then heated to 40° C. for being dissolved, 9 grams of potassium carbonate (65.07 mmol.) is added, 15 ml of benzyl chloride (130.13 mmol.) is added under stirring, heating reflux is performed for 1 hour, the reaction product is cooled to 50° C. after complete reaction is detected by TLC and then filtered while it is hot, the filtrate is put in a refrigerator for being cooled over night, crystals are separated out and pump-filtered, filter cakes are washed with 30 mL of absolute ethyl alcohol and then vacuum-dried to obtain 21.5 grams of white needle crystals, and the yield is 83.9%. for being dissolved heating reflux the reaction product is cooled to 50° C. after complete reaction filtered while it for being cooled over night crystals are separated out pump-filtered filter cakes are washed with 30 mL of absolute ethyl alcohol vacuum-dried

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.6 grams of 4-ethoxy-3-hydroxybenzaldehyde (100 mmol.) and 200 ml of absolute ethyl alcohol are added to a three-necked flask and then heated to 40° C. for being dissolved, 9 grams of potassium carbonate (65.07 mmol.) is added, 15 ml of benzyl chloride (130.13 mmol.) is added under stirring, heating reflux is performed for 1 hour, the reaction product is cooled to 50° C. after complete reaction is detected by TLC and then filtered while it is hot, the filtrate is put in a refrigerator for being cooled over night, crystals are separated out and pump-filtered, filter cakes are washed with 30 mL of absolute ethyl alcohol and then vacuum-dried to obtain 21.5 grams of white needle crystals, and the yield is 83.9%. for being dissolved heating reflux the reaction product is cooled to 50° C. after complete reaction filtered while it for being cooled over night crystals are separated out pump-filtered filter cakes are washed with 30 mL of absolute ethyl alcohol vacuum-dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-hydroxy-4-ethoxybenzaldehyde (0.350 g, 2.5 mmol), 3,4,5-trimethoxyacetophenone (0.443 mg, 2.5 mmol) and 50% w/v of aqueous sodium hydroxide (3.37 ml, 0.042 mol) in methanol (5 ml) at room temperature for 18 h. An orange solid was isolated by filtration, dissolved in ethyl acetate which was subsequently dried over MgSO4 and reduced in vacuo. Purification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) yielded 0.126 g (16.7%) of a yellow solid. 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.3 (m, 4H), 7.1 (dd, 1H), 6.9 (d, 1H), 5.75 (s, 1H), 4.2 (q, 2H), 3.95 (s×2, 9H), 1.5 (t, 3H). 13C-NMR (CDCl3) δ 190.0, 153.1, 150.0, 146.0, 133.7, 128.4. Mass Spectrum m/e (M+1) 359. Anal. Calcd. for C20H22O6: C, 67.03; H, 6.19. Found C, 66.74; H, 6.33. An orange solid was isolated by filtration was subsequently dried over MgSO4 Purification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Anhydrous potassium carbonate (2.25 g, 16.3 mmol) was added to 3,4-dihydroxybenzaldehyde (1.5 g, 10.8 mmol), in butanone (30 ml), at room temperature. The reaction was stirred for 10 min after which ethyl iodide (0.872 ml, 10.8 mmol) was added dropwise and the reaction was refluxed for 3 h. The reaction mixture was diluted with water and the product was extracted with dichloromethane (3×25 ml), the combined organic layers were dried over magnesium sulphate and reduced in vacuo. Purification by column chromatography (SiO2, petroleum:ether (40:60) with an increasing gradient of ethyl acetate) afforded 0.78 g (43%) of 3-hydroxy4-ethoxybenzaldehyde as a white solid. was added dropwise the reaction was refluxed for 3 h the product was extracted with dichloromethane (3×25 ml) the combined organic layers were dried over magnesium sulphate Purification by column chromatography (SiO2, petroleum:ether (40:60) with an increasing gradient of ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-hydroxy-4-ethoxybenzaldehyde (0.413 g, 2.5 mmol), 3,5-dimethoxyacetophenone (0.448 mg, 2.5 mmol) and 50% w/v of aqueous sodium hydroxide (3.98 ml, 0.049 mol) in methanol (5 ml) at room temperature for 18 h. The yellow solid that precipitated was filtered and sequentially washed with cold methanol and ether and finally dried in a vacuum dessicator. Purification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) yielded 0.29 g (36%) of a yellow solid. 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.2 (m, 2H), 7.1 (d, 3H), 6.8 (d, 1H), 6.5 (t, 1H), 5.7 (s, 1H), 4.1 (q, 2H), 3.9 (s, 6H), 1.4 (t, 3H). 13C-NMR (CDCl3) δ 190.1, 160.9, 148.2, 146.1, 144.9, 140.6, 128.5, 122.7, 120.3, 113.1, 111.4, 106.3, 105.0, 64.7, 55.7, 14.8. Mass Spectrum m/e (M+1) 329. Anal. Calcd. for C19H20O5.0.5H2O: C, 69.5; H, 6.14. Found C, 69.62; H, 6.16. The yellow solid that precipitated was filtered sequentially washed with cold methanol and ether finally dried in a vacuum dessicator Purification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-hydroxy-4-ethoxybenzaldehyde (0.413 g, 2.5 mmol), 3,5-dimethoxyacetophenone (0.448 mg, 2.5 mmol) and 50% w/v of aqueous sodium hydroxide (3.98 ml, 0.049 mol) in methanol (5 ml) at room temperature for 18 h. The yellow solid that precipitated was filtered and sequentially washed with cold methanol and ether and finally dried in a vacuum dessicator. Purification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) yielded 0.29 g (36%) of a yellow solid. 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.2 (m, 2H), 7.1 (d, 3H), 6.8 (d, 1H), 6.5 (t, 1H), 5.7 (s, 1H), 4.1 (q, 2H), 3.9 (s, 6H), 1.4 (t, 3H). 13C-NMR (CDCl3) δ 190.1, 160.9, 148.2, 146.1, 144.9, 140.6, 128.5, 122.7, 120.3, 113.1, 111.4, 106.3, 105.0, 64.7, 55.7, 14.8. Mass Spectrum m/e (M+1) 329. Anal. Calcd. for C19H20O5.0.5H2O: C, 69.5; H, 6.14. Found C, 69.62; H, 6.16. The yellow solid that precipitated was filtered sequentially washed with cold methanol and ether finally dried in a vacuum dessicator Purification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-hydroxy-4-ethoxybenzaldehyde (0.413 g, 2.5 mmol), 3,5-dimethoxyacetophenone (0.448 mg, 2.5 mmol) and 50% w/v of aqueous sodium hydroxide (3.98 ml, 0.049 mol) in methanol (5 ml) at room temperature for 18 h. The yellow solid that precipitated was filtered and sequentially washed with cold methanol and ether and finally dried in a vacuum dessicator. Purification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) yielded 0.29 g (36%) of a yellow solid. 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.2 (m, 2H), 7.1 (d, 3H), 6.8 (d, 1H), 6.5 (t, 1H), 5.7 (s, 1H), 4.1 (q, 2H), 3.9 (s, 6H), 1.4 (t, 3H). 13C-NMR (CDCl3) δ 190.1, 160.9, 148.2, 146.1, 144.9, 140.6, 128.5, 122.7, 120.3, 113.1, 111.4, 106.3, 105.0, 64.7, 55.7, 14.8. Mass Spectrum m/e (M+1) 329. Anal. Calcd. for C19H20O5.0.5H2O: C, 69.5; H, 6.14. Found C, 69.62; H, 6.16. The yellow solid that precipitated was filtered sequentially washed with cold methanol and ether finally dried in a vacuum dessicator Purification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Anhydrous potassium carbonate (2.25 g, 16.3 mmol) was added to 3,4-dihydroxybenzaldehyde (1.5 g, 10.8 mmol), in butanone (30 ml), at room temperature. The reaction was stirred for 10 min after which ethyl iodide (0.872 ml, 10.8 mmol) was added dropwise and the reaction was refluxed for 3 h. The reaction mixture was diluted with water and the product was extracted with dichloromethane (3×25 ml), the combined organic layers were dried over magnesium sulphate and reduced in vacuo. Purification by column chromatography (SiO2, petroleum:ether (40:60, v/v) with an increasing gradient of ethyl acetate) afforded 0.78 g (43%) of 3-hydroxy-4-ethoxybenzaldehyde as a white solid. was added dropwise the reaction was refluxed for 3 h the product was extracted with dichloromethane (3×25 ml) the combined organic layers were dried over magnesium sulphate Purification by column chromatography (SiO2, petroleum:ether (40:60