propyl 2-propoxybenzoate

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of Propyl 2-propoxy-benzoate (10 g, 240 mmol) in dimethyl sulfoxide (40 mL) was added potassium tert-butoxide (10 g, 890 mmol) in portions. The solution was heated to 70° C. on a water bath for 2 h, and the progress of the reaction was monitored by TLC using a hexane-ethyl acetate (8:2) solvent system. The reaction mass was cooled to 10° C., poured into ice water, and then acidified with 5% dilute hydrochloric acid. The precipitated solid was filtered and washed thoroughly with distilled water, and the crude mass was recrystallized in hexane (50 mL) to yield an off-white solid of 2-Propoxy-benzoic Acid (7.6 g, 80%). The reaction mass was cooled to 10° C. The precipitated solid was filtered washed thoroughly with distilled water the crude mass was recrystallized in hexane (50 mL)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of Propyl 2-propoxy-benzoate (10 g, 240 mmol) in dimethyl sulfoxide (40 mL) was added potassium tert-butoxide (10 g, 890 mmol) in portions. The solution was heated to 70° C. on a water bath for 2 h, and the progress of the reaction was monitored by TLC using a hexane-ethyl acetate (8:2) solvent system. The reaction mass was cooled to 10° C., poured into ice water, and then acidified with 5% dilute hydrochloric acid. The precipitated solid was filtered and washed thoroughly with distilled water, and the crude mass was recrystallized in hexane (50 mL) to yield an off-white solid of 2-Propoxy-benzoic Acid (7.6 g, 80%). The reaction mass was cooled to 10° C. The precipitated solid was filtered washed thoroughly with distilled water the crude mass was recrystallized in hexane (50 mL)

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

Procedure: A mixture of 3-hydroxybenzoic acid (10 g, 0.072 mol), potassium carbonate (22.0 g, 0.159 mol) and 1-iodopropane (20.5 ml, 35.7 g, 0.210 mol) in acetone (800 ml) was refluxed for 24 hours. The mixture was filtered, the filtrate was concentrated on the rotary evaporator and the concentrate was partitioned between water and diethyl ether. The aqueous layer was extracted with diethyl ether and the combined extracts were washed with saturated sodium bicarbonate solution and brine and then dried (MgSO4) and concentrated. Flash chromatography on silica gel (elution with 20-50% diethyl ether in n-hexane) gave propyl (3-propyloxy)benzoate. Yield 3.031 g. was refluxed for 24 hours The mixture was filtered the filtrate was concentrated on the rotary evaporator the concentrate was partitioned between water and diethyl ether The aqueous layer was extracted with diethyl ether the combined extracts were washed with saturated sodium bicarbonate solution and brine dried (MgSO4) concentrated