methyl 1,4-dihydroxynaphthalene-2-carboxylate

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

Procedure: Methyl 1,4-dihydroxynaphthalene-2-carboxylate (4.00 g, 18.3 mmol), 1-(4-diethylaminophenyl)-1-phenyl-prop-2-yn-1-ol (4.67 g, 18.3 mmol) and Al2O3 (4.5 g) in toluene (150 mL) was refluxed for 3 hrs, filtered whilst hot and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (20% hexane) as eluent followed by a second filtration through silica using DCM as eluent. The residue was crystallised from acetone-MeOH and the product isolated as a yellow solid (4.89 g, 56%) filtered whilst hot and the solvent removed under reduced pressure The residue was filtered through a short plug of silica followed by a second filtration through silica The residue was crystallised from acetone-MeOH

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

Procedure: A mixture of methyl 1,4-dihydroxynaphthalene-2-carboxylate (3.93 g, 18 mmol), 1-phenyl-1-(4-pyrrolidinophenyl)prop-2-yn-1-ol (5 g, 18 mmol) and Al2O3 (4 g) in PhMe (100 mL) was heated at reflux for 1.5 h, cooled, filtered, the residue washed with DCM and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (40% in hexanes) as eluent. The solvent was removed under reduced pressure and the residue was crystallized from Et2O-hexanes to give the title compound (5.47 g, 62%) as a yellow powder. was heated at reflux for 1.5 h cooled filtered the residue washed with DCM the solvent removed under reduced pressure The residue was filtered through a short plug of silica The solvent was removed under reduced pressure the residue was crystallized from Et2O-hexanes

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

Procedure: A mixture of methyl 1,4-dihydroxynaphthalene-2-carboxylate (3.93 g, 18 mmol), 1-phenyl-1-(4-pyrrolidinophenyl)prop-2-yn-1-ol (5 g, 18 mmol) and Al2O3 (4 g) in PhMe (100 mL) was heated at reflux for 1.5 h, cooled, filtered, the residue washed with DCM and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (40% in hexanes) as eluent. The solvent was removed under reduced pressure and the residue was crystallized from Et2O-hexanes to give the title compound (5.47 g, 62%) as a yellow powder. was heated at reflux for 1.5 h cooled filtered the residue washed with DCM the solvent removed under reduced pressure The residue was filtered through a short plug of silica The solvent was removed under reduced pressure the residue was crystallized from Et2O-hexanes

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

Procedure: 1,4-Dihydroxy-2-naphthoic acid (10 g, 49 mmol) and NaHCO3 (4.12 g, 49 mmol) was dissolved in DMF (dimethylformamide) (50 mL). Methyl iodide (6.96 g, 49 mmol) was added and the solution stirred at room temperature for 24 h, poured into water (1 L), filtered and washed with water to give the title compound (8.80 g, 82%) as a green powder. filtered washed with water

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

Procedure: 1,4-Dihydroxy-2-naphthoic acid (10 g, 49 mmol) and NaHCO3 (4.12 g, 49 mmol) was dissolved in DMF (dimethylformamide) (50 mL). Methyl iodide (6.96 g, 49 mmol) was added and the solution stirred at room temperature for 24 h, poured into water (1 L), filtered and washed with water to give the title compound (8.80 g, 82%) as a green powder. filtered washed with water