4-butoxy-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:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-hydroxy-4-butoxybenzaldehyde (1.0 g, 5.2 mmol), 3,4,5-trimethoxyacetophenone (1.08 g, 5.2 mmol) and 50% w/v of aqueous sodium hydroxide (8.25 ml, 0.103 mol) in methanol (10 ml) at room temperature for 18 h. An orange solid was isolated by filtration and was sequentially washed with cold methanol and ether and finally dried in a vacuum dessicator. Purification was achieved using column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) which gave 0.224 g (11.3%) of a yellow solid: 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.3 (m, 4H), 7.1 (dd, 1H), 6.9 (d, 1H), 5.7 (t, 1H), 5.7 (s, 1H), 4.1 (t, 2H), 4.0 (s×2, 9H), 1.8 (m, 2H), 1.5 (m, 2H), 1.0 (t, 3H). 13C-NMR (CDCl3) δ 189.1, 157.6, 153.2, 146.1, 144.7, 133.8, 122.9, 119.9, 112.7, 111.4, 106.1, 68.9, 60.9, 56.4, 31.2, 19.2, 15.01, 13.8. Mass Spectrum m/e (M+1) 387. Anal. Calcd. for C22H26O6: C, 68.38; H, 6.78. Found C, 68.57; H, 7.01. An orange solid was isolated by filtration was sequentially washed with cold methanol and ether finally dried in a vacuum dessicator Purification

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

Procedure: Anhydrous potassium carbonate (5.9 g, 0.0434 mmol) and sodium iodide (0.434 g, 2.9 mmol) were added to 3,4-dihydroxybenzaldehyde (4.0 g, 28.9 mmol), in butanone (100 ml), at room temperature. The reaction was stirred for 10 min after which butyl bromide (3.11 ml, 28.9 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 (3×50 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 2.25 g (58%) of 3-hydroxy-4-butoxybenzaldehyde as an off-white solid. was added dropwise the reaction was refluxed for 3 h the product was extracted with dichloromethane (3×50 ml) the combined organic layers were dried over magnesium sulphate 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-butoxybenzaldehyde (0.4 g, 2.1 mmol), 3,5-dimethoxyacetophenone (0.371.9, 2.1 mmol) and 50% w/v of aqueous sodium hydroxide (3.3 ml, 0.206 mol) in methanol (10 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 was achieved using column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) which gave 0.36 g (50%) of a yellow solid: 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.3 (m, 2H), 7.1 (d, 3H), 6.8 (d, 1H), 6.7 (t, 1H), 5.7 (s, 1H), 4.1 (t, 2H), 3.9 (s, 6H), 1.8 (m, 2H), 1.5 (m, 2H), 1.0 (t, 3H). 13C-NMR (CDCl3) δ 190.0, 160.9, 148.3, 146.0, 144.9, 140.5, 128.4, 122.6, 120.2, 112.9, 111.4, 106.2, 104.9, 68.8, 55.6, 31.1, 19.1. 13.7. Mass Spectrum m/e (M+1) 357. Anal. Calcd. for C21H24O5: C, 70.77, H, 6.79. Found C, 70.84; H, 6.81. The yellow solid that precipitated was filtered sequentially washed with cold methanol and ether finally dried in a vacuum dessicator Purification

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

Procedure: Anhydrous potassium carbonate (1.5 g, 5.4 mmol) and sodium iodide (0.108 g, 0.36 mmol) were added to 3,4-dihydroxybenzaldehyde (0.5 g, 3.6 mmol), In butanone (25 ml), at room temperature. The reaction was stirred for 10 min after which butyl bromide (0.777 ml, 3.6 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 0.5 g (71%) of 3-hydroxy-4-butoxybenzaldehyde as an off-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 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 (1.5 g, 5.4 mmol) and sodium iodide (0.108 g, 0.36 mmol) were added to 3,4-dihydroxybenzaldehyde (0.5 g, 3.6 mmol), In butanone (25 ml), at room temperature. The reaction was stirred for 10 min after which butyl bromide (0.777 ml, 3.6 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 0.5 g (71%) of 3-hydroxy-4-butoxybenzaldehyde as an off-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 v/v) with an increasing gradient of ethyl acetate)