Toluene → Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl ester

Participants

Reaction Conditions

Reaction Steps

First Step: 200.0 g of 1,4-dioxaspiro[4,5]decan-8-one (10), 301.4 g of ethyl diethylphosphonoacetate and 1,000 mL of toluene were added to a reactor under nitrogen atmosphere, and stirred at 5° C. 457.5 g of a 20% sodium ethoxide ethanol solution was added dropwise thereto at a temperature range of from 5 to 11° C. over 2 hours, followed by further stirring at 10° C. for 3 hours. After confirming that the reaction had been completed by GC analysis, the reaction mixture was poured into and mixed with 2,000 mL of water at 0° C. The mixture was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography using heptane as eluent, followed by distilling the solvent off under reduced pressure, to obtain 267.3 g of (1,4-dioxaspiro[4.5]dec-8-ylidene)acetic acid ethyl ester (11) as a pale yellow liquid.

Provenance & Evidence