Tetrahydrofuran → 2-(8-Phenyloctyl)benzaldehyde

) To a solution of N-[(2-methylphenyl)methylene]-1,1-dimethylethanamine (5.0 g, 0.03 mol) and N,N,N',N'-tetramethylethylene diamine (3.31 g, 0.03 mol) in tetrahydrofuran (40 mL), n-butyl lithium (2.5M, 11.4 mL, 0.03 mol) at 0° C. was slowly added. The solution was stirred for an additional 30 min followed by the quick addition of 1-bromo-7-phenylheptane (7.28 g, 0.03 mol) in tetrahydrofuran (10 mL). The reaction mixture was allowed to warm to room temperature and stirring was continued for 15 h. The reaction mixture was quenched with 10% aqueous hydrochloric acid (50 mL) and stirred for 30 min. The layers were separated, methylene chloride (50 mL) was added to the organic layer and the organics were washed with saturated brine solution (50 mL). The organics were then dried (magnesium sulfate), and concentrated to an oil to yield 2-(8-phenyloctyl)benzaldehyde (3.8 g, 45%): IR (neat film) 2920, 2880, 1695, 1600, 1455 cm-1 ; 1H NMR (CDCl3, 400 MHz) δ 10.25 (s, 1 H), 7.80 (dd, 1 H, J=1.2 and 7.7 Hz), 7.45 (m, 1 H), 7.33-7.13 (m, 7 H), 2.98 (t, 2 H, J=7.7 Hz), 2.58 (t, 2 H, J=7.7 Hz), 1.58 (m, 4 H), 1.30 (m, 8 H).

1. stirringstirring
2. waitwas continued for 15 h
3. customThe reaction mixture was quenched with 10% aqueous hydrochloric acid (50 mL)
4. stirringstirred for 30 min
5. customThe layers were separated
6. additionmethylene chloride (50 mL) was added to the organic layer
7. washthe organics were washed with saturated brine solution (50 mL)
8. dry with materialThe organics were then dried (magnesium sulfate)
9. concentrationconcentrated to an oil

ORD record

ord-9bdfb54d96fb49628e5690dc11f8b4dc

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05659084