Dimethylformamide → 3-(2-Hydroxyethyl)benzaldehyde

Temperature

-20 °C

A mixture 2-(3-bromophenyl)ethanol (1.00 g, 0.67 mL, 4.9 mmol) and N,N,N′,N′-tetramethylethylenediamine (1.5 mL) in anhydrous diethyl ether (10 mL) was cooled to −78° C. in a dry-ice acetone bath. n-Butyl lithium (2.4 M solution in hexanes, 4.0 mL, 9.8 mmol) was added dropwise and the resulting mixture was allowed to warm to −20° C. (over 1 h) and then cooled again to −78° C. Anhydrous N,N-dimethylformamide (5 mL) was added and the resulting mixture was allowed to reach room temperature and stirred for an additional 1 h. The reaction mixture was quenched with a saturated solution of ammonium chloride and the aqueous portion was extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by silica gel column chromatography using ethyl acetate-hexanes 2:3 as eluent to provide the desired compound as colorless oil. Yield: 88%.

1. temperaturecooled again to −78° C
2. customto reach room temperature
3. customThe reaction mixture was quenched with a saturated solution of ammonium chloride
4. extractionthe aqueous portion was extracted with ethyl acetate
5. washThe combined extracts were washed with brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by silica gel column chromatography

ORD record

ord-d6c6c5fe02874b09a4f15dbcdb1dd9fd

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530520B2