Carbon Dioxide → HCID 10942555, compound

Temperature

100 °C

To a suspension of 8.2 g of 60% sodium hydride in mineral oil in 271 mL of tetrahydrofuran at 0° C. with stirring under nitrogen was added dropwise 10 g of propargyl alcohol over 15 min. The mixture was stirred an additional 30 min. To the stirred mixture at 0° C was added 15.8 g of chloromethylmethyl ether. Stirring was continued at room temperature over night. The mixture was filtered and the solvent was removed from the filtrate. The residue was distilled (35-38° C., 4 mm) giving 8.5 g. of a liquid. The distillate was dissolved in 200 mL of ether. The solution was stirred under nitrogen and cooled to −78° C. as 34.1 mL of 2.5 molar n-butyl lithium in hexanes was added over 15 min. Stirring was continued for another 1.5 hr. Dry carbon dioxide was passed over the surface of the stirring reaction mixture as it warmed from −78° C. to room temperature. The mixture was stirred under a carbon dioxide atmosphere over night. The mixture was poured into a mixture of 14 mL of hydrochloric acid and 24 mL of water. The organic layer was separated and dried over magnesium sulfate. The solvent was removed and the residue was maintained at 100° C. at 4 mm for 1 hr giving 10.4 g of 4-methoxymethoxy-but-2-ynoic acid.

1. stirringThe mixture was stirred an additional 30 min
2. stirringStirring
3. waitwas continued at room temperature over night
4. filtrationThe mixture was filtered
5. customthe solvent was removed from the filtrate
6. distillationThe residue was distilled (35-38° C., 4 mm)
7. customgiving 8.5 g
8. stirringThe solution was stirred under nitrogen
9. additionwas added over 15 min
10. stirringStirring
11. temperaturewarmed from −78° C. to room temperature
12. stirringThe mixture was stirred under a carbon dioxide atmosphere over night
13. customThe organic layer was separated
14. dry with materialdried over magnesium sulfate
15. customThe solvent was removed

ORD record

ord-14c2f3d500f44430b1b27d7b8633cd1e

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06548496B2