methyl 5-hydroxy-2-methoxybenzoate

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

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

Procedure: Combine methyl 2-methoxy-5-hydroxybenzoate (0.37 g, 2.0 mmol) and a 1 M aqueous sodium hydroxide solution (20 mL, 20 mmol) in methanol (20 mL). After 2 hours, adjust the pH to about 2 using a 1 M aqueous hydrochloric acid solution and extract with dichloromethane. Dry the organic layer over MgSO4, filter, and evaporate in uacuo to give the title compound. extract with dichloromethane Dry the organic layer over MgSO4 filter evaporate in uacuo

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

Procedure: Combine methyl 2-methoxy-5-(t-butyldimethylsilyloxy)benzoate (11.1 g. 37.4 mmol) and ammonium fluoride (6.94 g, 0.187 mmol) in methanol (150 mL). Heat to reflux. After 1 hour, evaporate in vacuo to give a residue. Partition the residue between ethyl acetate and water, separate the layers, extract the organic layer with water and then brine. Dry the organic layer over MgSO4, filter, and evaporate in uacuo to give methyl 2-methoxy-5-hydroxybenzoate: mp; 110-112° C. Rf=0.27 (silica gel, 5% ethyl acetate/hexane). Heat to reflux evaporate in vacuo to give a residue Partition the residue between ethyl acetate and water separate the layers extract the organic layer with water Dry the organic layer over MgSO4 filter evaporate in uacuo

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

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

Procedure: Combine methyl 2-methoxy-5-(t-butyldimethylsilyloxy)benzoate (11.1 g. 37.4 mmol) and ammonium fluoride (6.94 g, 0.187 mmol) in methanol (150 mL). Heat to reflux. After 1 hour, evaporate in vacuo to give a residue. Partition the residue between ethyl acetate and water, separate the layers, extract the organic layer with water and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give methyl 2-methoxy-5-hydroxybenzoate: mp; 110-112° C. Rf=0.27 (silica gel, 5% ethyl acetate/hexane). Heat to reflux evaporate in vacuo to give a residue Partition the residue between ethyl acetate and water separate the layers extract the organic layer with water Dry the organic layer over MgSO4 filter evaporate in vacuo

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

Procedure: Combine methyl 2-methoxy-5-hydroxybenzoate (0.37 g, 2.0 mmol) and a 1 M aqueous sodium hydroxide solution (20 mL, 20 mmol) in methanol (20 mL). After 2 hours, adjust the pH to about 2 using a 1 M aqueous hydrochloric acid solution and extract with dichloromethane. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound. extract with dichloromethane Dry the organic layer over MgSO4 filter evaporate in vacuo

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

Procedure: Combine methyl 2-methoxy-5-hydroxybenzoate (0.37 g, 2.0 mmol) and a 1 M aqueous sodium hydroxide solution (20 mL, 20 mmol) in methanol (20 mL). After 2 hours, adjust the pH to about 2 using a 1 M aqueous hydrochloric acid solution and extract with dichloromethane. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound. extract with dichloromethane Dry the organic layer over MgSO4 filter evaporate in vacuo

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

Procedure: Combine methyl 2-methoxy-5-hydroxybenzoate (0.37 g, 2.0 mmol) and a 1 M aqueous sodium hydroxide solution (20 mL, 20 mmol) in methanol (20 mL). After 2 hours, adjust the pH to about 2 using a 1 M aqueous hydrochloric acid solution and extract with dichloromethane. Dry the organic layer over MgSO4, filter, and evaporate in uacuo to give the title compound. extract with dichloromethane Dry the organic layer over MgSO4 filter evaporate in uacuo

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

Procedure: Combine methyl 2-methoxy-5-(t-butyldimethylsilyloxy)benzoate (11.1 g. 37.4 mmol) and ammonium fluoride (6.94 g, 0.187 mmol) in methanol (150 mL). Heat to reflux. After 1 hour, evaporate in vacuo to give a residue. Partition the residue between ethyl acetate and water, separate the layers, extract the organic layer with water and then brine. Dry the organic layer over MgSO4, filter, and evaporate in uacuo to give methyl 2-methoxy-5-hydroxybenzoate: mp; 110-112° C. Rf=0.27 (silica gel, 5% ethyl acetate/hexane). Heat to reflux evaporate in vacuo to give a residue Partition the residue between ethyl acetate and water separate the layers extract the organic layer with water Dry the organic layer over MgSO4 filter evaporate in uacuo