methyl 3,7-dihydroxynaphthalene-2-carboxylate

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,7-dihydroxynaphthalene-2-carboxylic acid methyl ester (3.32 g, 15.5 mmol), bromoacetic acid tert-butyl ester (2.29 mL, 15.5 mmol) and potassium carbonate (4.28 g, 31.0 mmol) in DMF (20 mL) is stirred at 60° C. for 18 h. The reaction mixture is poured to EtOAc, wash with water and brine. It is then dried with MgSO4 and concentrated to give the title compound. wash with water and brine It is then dried with MgSO4 concentrated

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

Procedure: To a solution of 3,7-dihydroxynaphthalene-2-carboxylic acid (4.0 g, 19.6 mmol) in MeOH (80 mL) is added thionyl chloride (10 mL, 136 mmol) and it is stirred at RT for 48 h. The solvent is removed and purified to give the title compound. The solvent is removed purified

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

Procedure: To a solution of 3,7-dihydroxynaphthalene-2-carboxylic acid (4.0 g, 19.6 mmol) in MeOH (80 mL) is added thionyl chloride (10 mL, 136 mmol) and it is stirred at RT for 48 h. The solvent is removed and purified to give the title compound. The solvent is removed purified

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

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

Procedure: A suspension of methyl 3,7-dihydroxy-2-naphthoate (2.2 g; 10 mmole), benzylchloride (Merck) (1.26 mL; 11.0 mmole), potassium iodide (1.8 g; 11.0 mmole) and potassium carbonate (2.0 g; 15 mmole) in acetone (30 mL) was refluxed for 7 hours and then cooled to room temperature. The inorganic precipitate was filtered off and washed with acetone, whereas the filtrate was evaporated to dryness The solid residue was dissolved in ethyl acetate and the resulting solution was washed with 1M hydrochloric acid. After drying with sodium sulfate the organic layer was evaporated and the dry residue was recrystallized from methanol, whereat 1.2 g (39%) of methyl-7-benzyloxy-3-hydroxy-2-naphthoate were obtained. was refluxed for 7 hours The inorganic precipitate was filtered off washed with acetone, whereas the filtrate was evaporated to dryness The solid residue was dissolved in ethyl acetate the resulting solution was washed with 1M hydrochloric acid After drying with sodium sulfate the organic layer was evaporated the dry residue was recrystallized from methanol

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,7-dihydroxynaphthalene-2-carboxylic acid methyl ester (3.32 g, 15.5 mmol), bromoacetic acid tert-butyl ester (2.29 mL, 15.5 mmol) and potassium carbonate (4.28 g, 31.0 mmol) in DMF (20 mL) is stirred at 60° C. for 18 h. The reaction mixture is poured to EtOAc, wash with water and brine. It is then dried with MgSO4 and concentrated to give the title compound. wash with water and brine It is then dried with MgSO4 concentrated

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

Procedure: To a solution of 3,7-dihydroxynaphthalene-2-carboxylic acid (4.0 g, 19.6 mmol) in MeOH (80 mL) is added thionyl chloride (10 mL, 136 mmol) and it is stirred at RT for 48 h. The solvent is removed and purified to give the title compound. The solvent is removed purified