1-(2,6-dihydroxyphenyl)propan-1-one

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(2,6-bis-methoxymethoxy-phenyl)-propan-1-one (770 mg) in methanol (12 ml) and 1,4-dioxane (12 ml) was added 4N-HCl (2 ml) at room temperature, then the mixture was heated to 50° C. and stirred for 2 hours. The mixture was diluted with ethyl acetate and washed with water (20 ml) and brine (20 ml). The separated organic layer was dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography developed by hexane-ethyl acetate. 1-(2,6-dihydroxyphenyl)-propan-1-one was obtained as a yellow solid (398 mg). EI-MS: m/z 178 (M+); 1H-NMR (CDCl3): δ 1.03-1.08 (2H, m), 1.29-1.35 (2H, m), 2.21-2.31 (1H, m), 6.41 (2H, d, J=8.3 Hz), 7.23 (1H, t, J=8.3 Hz) 9.24 (2H, brs). washed with water (20 ml) and brine (20 ml) The separated organic layer was dried over anhydrous magnesium sulfate evaporated The residue was purified by silica gel column chromatography

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

Procedure: A solution of hydroxylamine hydrochloride (510 mg, 7.3 mmol) and sodium acetate trihydrate (629 mg, 4.6 mmol) dissolved in 20 ml of a mixture EtOH/H2O (7/3) was added to a solution of 1-(2,6-dihydroxyphenyl)-1-propanone (Intermediate 28, 1.0 g) in 15 ml of a mixture EtOH/H2O (7/3). After refluxing and stirring under N2 overnight, additional hydroxylamine hydrochloride (510 mg, 7.3 mmol) and sodium acetate trihydrate (629 mg, 4.6 mmol) dissolved in 4.5 mL of water were added. The reaction mixture was heated at reflux an additional 3 hours. After cooling down to room temperature, the volatiles were removed. Then water was added and reaction mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound (1.05 g). After refluxing were added The reaction mixture was heated at reflux an additional 3 hours the volatiles were removed Then water was added reaction mixture was extracted with ethyl acetate The gathered organic layers were dried over sodium sulphate filtered evaporated

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

Procedure: 1-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)-1-propanone (Intermediate 27, 1.7 g) was dissolved in methanol (50.0 ml) and an aqueous solution of HCl (26.7 ml, 53.5 mmol of a 2M aqueous solution) was added. The reaction mixture was refluxed for 2 hours. After quenching with water, the reaction mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound (1.11 g). The reaction mixture was refluxed for 2 hours After quenching with water the reaction mixture was extracted with ethyl acetate The gathered organic layers were dried over sodium sulphate filtered evaporated

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

Procedure: 1-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)-1-propanone (Intermediate 27, 1.7 g) was dissolved in methanol (50.0 ml) and an aqueous solution of HCl (26.7 ml, 53.5 mmol of a 2M aqueous solution) was added. The reaction mixture was refluxed for 2 hours. After quenching with water, the reaction mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound (1.11 g). The reaction mixture was refluxed for 2 hours After quenching with water the reaction mixture was extracted with ethyl acetate The gathered organic layers were dried over sodium sulphate filtered evaporated

Conditions: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100 mL round bottom flask is added 2′,6′ dihydroxypropiophenone (25 g, 0.15 mol) and to it is then added dichloromethane (50 mL). This is then cooled to −75° C. and then 2.6 mL of H3PO4 is added to it followed by 6.22 mL of boron trifluoride etherate and then isobutylene (125 mL). The reaction is then stirred at −75° C. for 1.5 hrs and then at room temperature overnight. The reaction mixture is then poured into a 2N ammonium hydroxide solution (200 mL) and extracted with dichloromethane. The organic layer is then washed with water and then with brine and dried over sodium sulfate and filtered. The crude residue obtained after concentration of the filtrate is purified by flash chromatography using silica gel (ethyl acetate:hexanes) to afford the above product. at room temperature overnight extracted with dichloromethane The organic layer is then washed with water with brine and dried over sodium sulfate filtered

Conditions: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100 mL round bottom flask is added 2′,6′ dihydroxypropiophenone (25 g, 0.15 mol) and to it is then added dichloromethane (50 mL). This is then cooled to −75° C. and then 2.6 mL of H3PO4 is added to it followed by 6.22 mL of boron trifluoride etherate and then isobutylene (125 mL). The reaction is then stirred at −75° C. for 1.5 hrs and then at room temperature overnight. The reaction mixture is then poured into a 2N ammonium hydroxide solution (200 mL) and extracted with dichloromethane. The organic layer is then washed with water and then with brine and dried over sodium sulfate and filtered. The crude residue obtained after concentration of the filtrate is purified by flash chromatography using silica gel (ethyl acetate:hexanes) to afford the above product. at room temperature overnight extracted with dichloromethane The organic layer is then washed with water with brine and dried over sodium sulfate filtered

Conditions: temp:-75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100 mL round bottom flask is added 2′,6′dihydroxypropiophenone (25 g, 0.15 mol) and to it is then added dichloromethane (50 mL). This is then cooled to −75° C. and then 2.6 mL of H3PO4 is added to it followed by 6.22 mL of boron trifluoride etherate and then isobutylene (125 mL). The reaction is then stirred at −75° C. for 1.5 hrs and then at room temperature overnight. The reaction mixture is then poured into a 2N ammonium hydroxide solution (200 mL) and extracted with dichloromethane. The organic layer is then washed with water and then with brine and dried over sodium sulfate and filtered. The crude residue obtained after concentration of the filtrate is purified by flash chromatography using silica gel (ethyl acetate:hexanes) to afford the above product. at room temperature overnight extracted with dichloromethane The organic layer is then washed with water with brine and dried over sodium sulfate filtered

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(2,6-bis-methoxymethoxy-phenyl)-propan-1-one (770 mg) in methanol (12 ml) and 1,4-dioxane (12 ml) was added 4N-HCl (2 ml) at room temperature, then the mixture was heated to 50° C. and stirred for 2 hours. The mixture was diluted with ethyl acetate and washed with water (20 ml) and brine (20 ml). The separated organic layer was dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography developed by hexane-ethyl acetate. 1-(2,6-dihydroxyphenyl)-propan-1-one was obtained as a yellow solid (398 mg). EI-MS: m/z 178 (M+); 1H-NMR (CDCl3): δ 1.03-1.08 (2H, m), 1.29-1.35 (2H, m), 2.21-2.31 (1H, m), 6.41 (2H, d, J=8.3 Hz), 7.23 (1H, t, J=8.3 Hz) 9.24 (2H, brs). washed with water (20 ml) and brine (20 ml) The separated organic layer was dried over anhydrous magnesium sulfate evaporated The residue was purified by silica gel column chromatography

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

Procedure: A solution of hydroxylamine hydrochloride (510 mg, 7.3 mmol) and sodium acetate trihydrate (629 mg, 4.6 mmol) dissolved in 20 ml of a mixture EtOH/H2O (7/3) was added to a solution of 1-(2,6-dihydroxyphenyl)-1-propanone (Intermediate 28, 1.0 g) in 15 ml of a mixture EtOH/H2O (7/3). After refluxing and stirring under N2 overnight, additional hydroxylamine hydrochloride (510 mg, 7.3 mmol) and sodium acetate trihydrate (629 mg, 4.6 mmol) dissolved in 4.5 mL of water were added. The reaction mixture was heated at reflux an additional 3 hours. After cooling down to room temperature, the volatiles were removed. Then water was added and reaction mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound (1.05 g). After refluxing were added The reaction mixture was heated at reflux an additional 3 hours the volatiles were removed Then water was added reaction mixture was extracted with ethyl acetate The gathered organic layers were dried over sodium sulphate filtered evaporated

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

Procedure: 1-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)-1-propanone (Intermediate 27, 1.7 g) was dissolved in methanol (50.0 ml) and an aqueous solution of HCl (26.7 ml, 53.5 mmol of a 2M aqueous solution) was added. The reaction mixture was refluxed for 2 hours. After quenching with water, the reaction mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound (1.11 g). The reaction mixture was refluxed for 2 hours After quenching with water the reaction mixture was extracted with ethyl acetate The gathered organic layers were dried over sodium sulphate filtered evaporated