Sodium Hydroxide → 3-(3-Fluoro-4-methylphenyl)-2,2-dimethylpropanal

Temperatur

70 °C

Under argon, a mixture of sodium hydroxide (2.8 g, 70 mmol) and tetrabutylammonium iodide (0.6 g, 1.6 mmol) in 8 ml benzene and 2.8 ml H2O was heated at 70° C. to form a homogeneous mixture. A mixture of the product of STEP 2 (10.5 g, 60.1 mmol) and isobutylaldehyde (5.76 g, 80 mmol) in 20 ml benzene was added to the above solution dropwise. The resulting mixture was heated at 70-75° C. for 6 h and cooled to room temperature. The product was extracted with ethyl acetate and washed with H2O. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried with MgSO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=5/95) to yield a colorless oil in 7.3 g. NMR spectra of the product were consistent for the proposed structure.

1. customto form a homogeneous mixture
2. additionwas added to the above solution dropwise
3. temperatureThe resulting mixture was heated at 70-75° C. for 6 h
4. temperaturecooled to room temperature
5. extractionThe product was extracted with ethyl acetate
6. washwashed with H2O
7. extractionThe aqueous layer was extracted with ethyl acetate
8. washThe combined organic layer was washed with brine
9. dry with materialdried with MgSO4
10. concentrationconcentrated
11. customThe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=5/95)
12. customto yield a colorless oil in 7.3 g

ORD-Eintrag

ord-6c9f69a2b4cd49bd9926e3333bb46ab0

Quelldatensatz

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06531494B1