Acetic Acid → Methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylate

4-cyano-4-phenyl heptane dicarboxylic acid dimethylester (19.8 g, 68 mmol) was dissolved in dry tetrahydrofuran (480 mL). Potassium tert-butylate (13.2 g, 120 mmol) was then added in portions. During this addition the reaction mixture changed colour to orange. The batch was then boiled for 5 h with reflux. A brown solution was formed during boiling. The reaction mixture was cooled to room temperature overnight. 2.5N acetic acid (230 mL) was slowly added in drops to the reaction mixture with ice cooling. The batch was then mixed with toluol (100 mL), the organic phase separated and washed with saturated NaHCO3 solution (3×100 mL), H2O (3×50 mL) and NaCl solution (1×100 mL). After drying with Na2SO4 the solvent was distilled off in a vacuum. A yellowish solid remained.

1. additionDuring this addition the reaction mixture
2. temperaturewith reflux
3. customA brown solution was formed
4. customthe organic phase separated
5. washwashed with saturated NaHCO3 solution (3×100 mL), H2O (3×50 mL) and NaCl solution (1×100 mL)
6. dry with materialAfter drying with Na2SO4 the solvent
7. distillationwas distilled off in a vacuum

ORD-Eintrag

ord-77c11b1555894894baf067a9c69607c1

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08835689B2