Acetone → Diethyl 2,2-dimethyl-1,3-dioxane-5,5-dicarboxylate

To a clear solution of diethyl bis(hydroxymethyl)malonate in 478 mL (6.52 mol) of acetone and 478 mL (8.45 mol) of acetone dimethylacetal was added 1.1 mL (42 mmol) of concentrated sulfuric acid and the reaction was stirred at room temperature overnight (19 hours). After 120 mL of saturated sodium carbonate was added, the mixture was stirred at room temperature for 15 minutes. The layers were separated and the semi-crystalline residue was washed with acetone (2×250 mL). The organics were evaporated. The residue was dispersed in 500 mL of ether and 250 mL of saturated Na2CO3, and stirred for 20 minutes. After the layers were separated, the organic layer was stirred with 250 mL of brine for 5 minutes and the layers separated. The organic layer was dried, evaporated, and placed under vacuum for 3 hours to produce a colorless oil, 527.5 g, in 94% yield.

1. stirringthe mixture was stirred at room temperature for 15 minutes
2. customThe layers were separated
3. washthe semi-crystalline residue was washed with acetone (2×250 mL)
4. customThe organics were evaporated
5. additionThe residue was dispersed in 500 mL of ether
6. stirring250 mL of saturated Na2CO3, and stirred for 20 minutes
7. customAfter the layers were separated
8. stirringthe organic layer was stirred with 250 mL of brine for 5 minutes
9. customthe layers separated
10. customThe organic layer was dried
11. customevaporated
12. waitplaced under vacuum for 3 hours
13. customto produce a colorless oil, 527.5 g

ORD-Eintrag

ord-ac182ccefd504c54a1887713f6c1288c

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09024028B2