2-hydroxy-4-(3-methylbut-2-enoxy)benzaldehyde

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

Procedure: 10.6 g (206 mmol) of 2-hydroxy-4-(3methylbut-2-enyloxy)benzaldehyde and 5.4 ml of dimethyl sulfate were dissolved in 102 ml of distilled acetone, the solution was added 25.5 g of potassium carbonate, and the resulting mixture was refluxed for 5 hours. The mixture was filtered and the filtrate concentrated in vacuo to give 8.3 g of an yellow oil from which 5.4 g of 2-methoxy-4-(3-methylbut-2-enyloxy)benzaldehyde was isolated by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 400 g) using petroleum ether-ethyl acetate (9:1, 1000 ml), (4:1, 500 ml) as eluents. the resulting mixture was refluxed for 5 hours The mixture was filtered the filtrate concentrated in vacuo

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

Procedure: 10.6 g (206 mmol) of 2-hydroxy-4-(3methylbut-2-enyloxy)benzaldehyde and 5.4 ml of dimethyl sulfate were dissolved in 102 ml of distilled acetone, the solution was added 25.5 g of potassium carbonate, and the resulting mixture was refluxed for 5 hours. The mixture was filtered and the filtrate concentrated in vacuo to give 8.3 g of an yellow oil from which 5.4 g of 2-methoxy-4-(3-methylbut-2-enyloxy)benzaldehyde was isolated by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 400 g) using petroleum ether-ethyl acetate (9:1, 1000 ml), (4:1, 500 ml) as eluents. the resulting mixture was refluxed for 5 hours The mixture was filtered the filtrate concentrated in vacuo

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

Procedure: 10.6 g (206 mmol) of 2-hydroxy4-(3-methylbut-2-enyloxy)benzaldehyde and 5.4 ml of dimethyl sulfate were dissolved in 102 ml of distilled acetone, the solution was added 25.5 g of potassium carbonate, and the resulting mixture was refluxed for 5 hours. The mixture was filtered and the filtrate concentrated in vacuo to give 8.3 g of an yellow oil from which 5.4 g of 2-methoxy4-(3-methylbut-2enyloxy)benzaldehyde was isolated by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 400 g) using petroleum ether-ethyl acetate (9:1, 1000 ml), (4:1, 500 ml) as eluents. the resulting mixture was refluxed for 5 hours The mixture was filtered the filtrate concentrated in vacuo

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

Procedure: A solution of 6 g (0.11 mol) of potassium hydroxide, 22.7 g (0.1 mol) of benzyltriethylammonium chloride, and 14 g (0.1 mol) of 2,4-dihydroxybenzaldehyde was concentrated in vacuo. The residue was suspended in 100 ml of ethyl acetate and 11.7 ml (0.1 mol) of dimethylallyl bromide was slowlv added to the solution. The mixture was extracted with 100 ml of water, and the organic phase was dried and concentrated in vacuo to give 3.568 g of a residue, from which 4.738 g (20%) of 4-(3-methyl)-but-2-enyloxy-2-hydroxybenzaldehyde identical to that previously described by S. Khan, and M. Krishnamurti in Indian J. Chem. 22B (1983), 276 was purified by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 200 g) using petroleum ether-ethyl acetate (9:1) as an eluent. The mixture was extracted with 100 ml of water the organic phase was dried concentrated in vacuo

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

Procedure: 10.6 g (206 mmol) of 2-hydroxy-4-(3methylbut-2-enyloxy)benzaldehyde and 5.4 ml of dimethyl sulfate were dissolved in 102 ml of distilled acetone, the solution was added 25.5 g of potassium carbonate, and the resulting mixture was refluxed for 5 hours. The mixture was filtered and the filtrate concentrated in vacuo to give 8.3 g of an yellow oil from which 5.4 g of 2-methoxy-4-(3-methylbut-2-enyloxy)benzaldehyde was isolated by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 400 g) using petroleum ether-ethyl acetate (9:1, 1000 ml), (4:1, 500 ml) as eluents. the resulting mixture was refluxed for 5 hours The mixture was filtered the filtrate concentrated in vacuo