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

Temperature

5 °C

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.

1. stirringby further stirring at 10° C. for 3 hours
2. additionthe reaction mixture was poured into and
3. customThe mixture was separated into an organic layer
4. extractionextraction to the organic layer
5. washwashed with water
6. dry with materialby drying over anhydrous magnesium sulfate
7. customThereafter, the solvent was removed by distillation under reduced pressure
8. customthe resulting residue was purified by silica gel column chromatography
9. distillationby distilling the solvent off under reduced pressure

ORD record

ord-a6083e81a01643d0841d43c181bf2951

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07510749B2