Hexane → 1-(2,2-Diethoxyethoxy)-4-fluorobenzene

Temperature

25 °C

A solution of 4-fluorophenol (28.1 g., 0.25 mole) in dry dimethylformamide (30 ml.) is added dropwise to a suspension of hexane (2 × 30 ml.) -- prewashed sodium hydride (50% dispersion in mineral oil, 12.5 g., 0.26 mole) in dry dimethylformamide (120 ml.). After stirring at 25° C. for 10 minutes, the reaction mixture is treated with bromoacetaldehyde diethyl acetal (49.3 g., 0.25 mole) and heated at 100° C. for 4 hours. Upon cooling to 25° C., the reaction mixture is filtered to remove insoluble sodium bromide. The filtrate is evaporated in vacuo, leaving an oily residue which is triturated with acetone (100 ml.) at 25° C. and filtered to remove additional sodium bromide. Evaporation of the filtrate in vacuo provides a residual oil which is distilled to afford the title compound as a colorless oil (46.7 g., 82%), bp0.05 87° C.; pmr (CCl 4) δ 1.17 (6H, t), 3.57 (2H, q), 3.61 (2H, q), 3.85 (2H, d), 4.68 (H, t) and 6.6-7.1 (4H, m).

1. temperatureheated at 100° C. for 4 hours
2. temperatureUpon cooling to 25° C.
3. filtrationthe reaction mixture is filtered
4. customto remove insoluble sodium bromide
5. customThe filtrate is evaporated in vacuo
6. customleaving an oily residue which
7. customis triturated with acetone (100 ml.) at 25° C.
8. filtrationfiltered
9. customto remove additional sodium bromide
10. customEvaporation of the filtrate in vacuo
11. customprovides a residual oil which
12. distillationis distilled

ORD record

ord-afc5a4e8f90042ddae3ee06af325ad52

Source dataset

uspto-grants-1977_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04022794