3-Hydroxybenzaldehyde → 3-[2-(2-Methoxyethoxy)ethoxy]benzaldehyde

Temperature

57 °C

To a solution of 3-hydroxybenzaldehyde (5.0 g, 41 mmol) in N,N-dimethylformamide (100 mL) was added bromo-2-(2-methoxyethoxy)ethane (6.0 mL, 45 mmol) followed by addition of solid potassium carbonate (17 g, 122 mmol). The resulting slurry was heated under nitrogen at 57° C. for 19 h. The reaction mixture was cooled to room temperature and filtered. The filter cake was washed with methanol and the filtrate was reduced in vacuo to ˜50 mL and poured into water (200 mL). The solution was acidified to pH˜4 with hydrochloric acid (1 M) and extracted with ethyl acetate (3×150 mL). The combined organic layer was washed with aqueous copper sulphate (75 mL), water (100 mL) and brine (100 mL), dried over sodium sulphate, filtered and concentrated in vacuo to a viscous oil. The oil was dried in vacuo to give 9,3 g (99% yield) of the title compound as a tan oil. 1HNMR (300 MHz, DMSO-d6, TFA-d) δ 9.98 (s, 1H), 7.51 (m, 2H), 7.44 (s, 1H), 7.30 (m, 1H), 4.18 (t J=5 Hz, 2H), 3.76 (t, J=5 Hz, 2H), 3.60 (t, J=5 Hz, 2H), 3.46 (t, J=5 Hz, 2H), 3.25 (s, 3H).

1. temperatureThe reaction mixture was cooled to room temperature
2. filtrationfiltered
3. washThe filter cake was washed with methanol
4. additionpoured into water (200 mL)
5. extractionextracted with ethyl acetate (3×150 mL)
6. washThe combined organic layer was washed with aqueous copper sulphate (75 mL), water (100 mL) and brine (100 mL)
7. dry with materialdried over sodium sulphate
8. filtrationfiltered
9. concentrationconcentrated in vacuo to a viscous oil
10. customThe oil was dried in vacuo

ORD record

ord-b9f5424a1c304766a57a3d27287e2aba

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07205314B2