Sodium Hydroxide → Methyl 4-oxodecanoate

Participants

Reaction Conditions

Reaction Steps

To the resulting isobutyl 4-oxodecanoate were added 1 L of methanol and 250 g of 25% sodium hydroxide, and the mixture was stirred at 25° C. for 1 hour, followed by distilling off methanol in vacuo. Subsequently, thereto were added 2 L of water and 1 L of toluene. The resulting mixture was stirred at room temperature for 1 hour and then allowed to stand to separate the water phase. To the water phase were added 175 g of concentrated hydrochloric acid and 1.8 L of toluene. The resulting mixture was stirred for 10 minutes and then allowed to stand to separate the organic phase. Toluene in the organic phase was distilled off in vacuo and 1 L of toluene and 47.5 mL of concentrated sulfuric acid were added. The resulting mixture was heated under reflux for 1 hour and then cooled to 25° C. Thereto was gradually added 155 g of sodium hydrogencarbonate followed by stirring for 10 minutes at 25° C. Methanol was distilled off in vacuo and then 3 L of water and 1.8 L of toluene were added. The resulting mixture was stirred for 10 minutes at room temperature and then allowed to stand to separate the organic phase. Toluene in the organic phase was distilled off, yielding methyl 4-oxodecanoate (a compound in which R17 represents an n-pentyl group, and R18 represents a methyl group in the above formula (12)). Gas chromatographic analysis showed that the yield of methyl 4-oxodecanoate relative to isobutyl 4-oxodecanoate was 95%.

Provenance & Evidence