4-oxononanoic acid

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

Procedure: A solution of 20 g 4-oxo-nonanoic acid, 19.3 g geraniol, 26.8 g N,N-dicyclohexyl-carbodiimide and 1.0 g 4-pyrrolidinopyridine in 300 ml of dichloromethane was stirred for 24 hours at room temperature. The precipitate was filtered off, the filtrate was diluted with ether, washed with aqueous hydrochloric acid, saturated NaHCO3 and brine. The organic phase was dried, filtered and evaporated to dryness. The resulting oil-crystal mixture was purified by chromatography to yield 21.4 g of a colorless oil. The precipitate was filtered off the filtrate was diluted with ether washed with aqueous hydrochloric acid, saturated NaHCO3 and brine The organic phase was dried filtered evaporated to dryness The resulting oil-crystal mixture was purified by chromatography

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

Procedure: The part (a) ester (1.0 g, 3.7 mmol) was treated with a solution of NaOH (1.5 g, 37.5 mmol) in water (15 ml). The heterogeneous mixture was heated under gentle reflux for 9 hours. After cooling, ether (20 ml) was added. The layers were separated. The aqueous layer was washed with ether (10 ml) and then acidified to pH 2 using concentrated HCl. The product was extracted into ether (3×20 ml). The ether extracts were washed with saturated NaCl solution, dried (MgSO4), and freed of solvent in vacuo leaving an oil which gradually solidified (345 mg). This was crystallized from petroleum ether to give title acid (189.9 mg, 30%) as colorless needles, m.p. 64°-66° C. The heterogeneous mixture was heated under gentle reflux for 9 hours After cooling The layers were separated The aqueous layer was washed with ether (10 ml) The product was extracted into ether (3×20 ml) The ether extracts were washed with saturated NaCl solution dried (MgSO4) leaving an oil which This was crystallized from petroleum ether to give title acid (189.9 mg, 30%) as colorless needles, m.p. 64°-66° C.

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

Procedure: A solution of 20 g 4-oxo-nonanoic acid, 19.3 g geraniol, 26.8 g N,N-dicyclohexyl-carbodiimide and 1.0 g 4-pyrrolidinopyridine in 300 ml of dichloromethane was stirred for 24 hours at room temperature. The precipitate was filtered off, the filtrate was diluted with ether, washed with aqueous hydrochloric acid, saturated NaHCO3 and brine. The organic phase was dried, filtered and evaporated to dryness. The resulting oil-crystal mixture was purified by chromatography to yield 21.4 g of a colorless oil. The precipitate was filtered off the filtrate was diluted with ether washed with aqueous hydrochloric acid, saturated NaHCO3 and brine The organic phase was dried filtered evaporated to dryness The resulting oil-crystal mixture was purified by chromatography

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

Procedure: A solution of 20 g 4-oxo-nonanoic acid, 19.3 g geraniol, 26.8 g N,N-dicyclohexyl-carbodiimide and 1.0 g 4-pyrrolidinopyridine in 300 ml of dichloromethane was stirred for 24 hours at room temperature. The precipitate was filtered off, the filtrate was diluted with ether, washed with aqueous hydrochloric acid, saturated NaHCO3 and brine. The organic phase was dried, filtered and evaporated to dryness. The resulting oil-crystal mixture was purified by chromatography to yield 21.4 g of a colorless oil. The precipitate was filtered off the filtrate was diluted with ether washed with aqueous hydrochloric acid, saturated NaHCO3 and brine The organic phase was dried filtered evaporated to dryness The resulting oil-crystal mixture was purified by chromatography

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

Procedure: A solution of 20 g 4-oxo-nonanoic acid, 19.3 g geraniol, 26.8 g N,N-dicyclohexyl-carbodiimide and 1.0 g 4-pyrrolidinopyridine in 300 ml of dichloromethane was stirred for 24 hours at room temperature. The precipitate was filtered off, the filtrate was diluted with ether, washed with aqueous hydrochloric acid, saturated NaHCO3 and brine. The organic phase was dried, filtered and evaporated to dryness. The resulting oil-crystal mixture was purified by chromatography to yield 21.4 g of a colorless oil. The precipitate was filtered off the filtrate was diluted with ether washed with aqueous hydrochloric acid, saturated NaHCO3 and brine The organic phase was dried filtered evaporated to dryness The resulting oil-crystal mixture was purified by chromatography

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

Procedure: The part (a) ester (1.0 g, 3.7 mmol) was treated with a solution of NaOH (1.5 g, 37.5 mmol) in water (15 ml). The heterogeneous mixture was heated under gentle reflux for 9 hours. After cooling, ether (20 ml) was added. The layers were separated. The aqueous layer was washed with ether (10 ml) and then acidified to pH 2 using concentrated HCl. The product was extracted into ether (3×20 ml). The ether extracts were washed with saturated NaCl solution, dried (MgSO4), and freed of solvent in vacuo leaving an oil which gradually solidified (345 mg). This was crystallized from petroleum ether to give title acid (189.9 mg, 30%) as colorless needles, m.p. 64°-66° C. The heterogeneous mixture was heated under gentle reflux for 9 hours After cooling The layers were separated The aqueous layer was washed with ether (10 ml) The product was extracted into ether (3×20 ml) The ether extracts were washed with saturated NaCl solution dried (MgSO4) leaving an oil which This was crystallized from petroleum ether to give title acid (189.9 mg, 30%) as colorless needles, m.p. 64°-66° C.