Tetrahydrofuran → 2-(8-Phenyloctyl)benzaldehyde

Temperature

50 °C

To a stirred solution of N-[(2-methylphenyl)methylene]-1,1-dimethylethanamine (21.0 g, 0.12 mol) in tetrahydrofuran (75 mL), n-BuLi (1.54M, 78 mL, 0.12 mol) was added over 1 h such that the temperature was maintained between 20°-30° C. with cooling. The mixture was stirred for 30 min and 1-chloro-7-phenylheptane (21.05 g, 0.1 mol) in tetrahydrofuran (40 mL) was added quickly. The mixture was heated at 50° C. for 3 h and quenched by the slow addition of dilute hydrochloric acid. Hydrolysis was completed by heating the mixture at 50°-60° C. for 2.5 h. The mixture was cooled to ambient temperature and the organic phase separated. The aqueous phase was extracted with hexane, and the combined organic extracts were washed with water. The extracts were dried over magnesium sulphate and, after filtering and washing the filter cake with hexane, the organic solution was concentrated under vacuum to give 2-(8-phenyloctyl)benzaldehyde as an oil (34.56 g, 65.3% pure by HPLC assay, 77% corrected yield).

1. temperaturewas maintained between 20°-30° C.
2. temperaturewith cooling
3. customquenched by the slow addition of dilute hydrochloric acid
4. customHydrolysis
5. temperatureby heating the mixture at 50°-60° C. for 2.5 h
6. temperatureThe mixture was cooled to ambient temperature
7. customthe organic phase separated
8. extractionThe aqueous phase was extracted with hexane
9. washthe combined organic extracts were washed with water
10. dry with materialThe extracts were dried over magnesium sulphate
11. filtrationafter filtering
12. washwashing the filter cake with hexane
13. concentrationthe organic solution was concentrated under vacuum
14. customto give

ORD record

ord-f28a481d9c56436698f780293eaca7d8

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05659084