Ethylene Glycol → 2,2-Dimethyl-3-phenylpropanoic acid

Temperature

196 °C

A solution of 2,2-dimethyl-3-phenylpropanenitrile (1.0 g, 6.28 mmol) in ethylene glycol (5 mL) was treated with solid potassium hydroxide (1.06 g, 18.84 mmol). The reaction mixture was stirred for 48 h at 196° C. under a nitrogen atmosphere. Ethylene glycol was removed under vacuum distillation. 1 N Sodium hydroxide solution (25 mL) and ethyl acetate (15 mL) were added to the brown residue. The layers were separated, and the aqueous layer was extracted with ethyl acetate (375 mL). The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated under reduced pressure to give 0.856 g (76%) of 2,2-dimethyl-3-phenylpropanoic acid. 1H NMR (DMSO-d6, 400 MHz) δ 12.20 (s, 1H), 7.28-7.24 (m, 2H), 7.22-7.20 (m, 1H), 7.15-7.13 (m, 2H), 2.78 (s, 2H), 1.07 (s, 6H). This compound was used in subsequent reaction with out further analysis.

1. customEthylene glycol was removed under vacuum distillation
2. addition1 N Sodium hydroxide solution (25 mL) and ethyl acetate (15 mL) were added to the brown residue
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with ethyl acetate (375 mL)
5. washThe combined organic layers were washed with water and brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. customevaporated under reduced pressure

ORD record

ord-0b880b510097450a9408fea4d0f362d9

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06660744B1