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

온도

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 reaction mixture was heated at 70-75° C. for 6 h. 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 (58%). 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. customThe resulting reaction mixture
4. temperaturewas heated at 70-75° C. for 6 h
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 (58%)

ORD 기록

ord-f1b8e0cccaa84d908eda69bb203afa75

출처 데이터셋

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06531494B1