4-Hydroxybenzaldehyde → 4-(3-Chloropropoxy)-benzaldehyde

To a suspension of sodium hydride (50% in oil, 3.9 g, 82 mmol) in dimethylformamide (100 ml) was added p-hydroxybenzaldehyde (5.0 g, 41 mmol). The mixture was stirred at room temperature under an atmosphere of nitrogen for one hour, then treated dropwise with 1-bromo-3-chloropropane (8.1 ml, 82 mmol). The mixture was stirred at room temperature for 12 hours, quenched with methanol and filtered through Celite. The filtrate was dissolved in diethyl ether (500 ml), washed with water (3×200 ml) and dried over Na2 SO4. The ether layer was concentrated to give 6.1 g (80% yield) of 4-chloropropoxybenzaldehyde as a yellow liquid. 1H NMR (CDCl3): δ 9.95 (s, 1H), 7.85 (d, J=8.1 Hz, 2H), 7.01 (d, J=8.1 Hz, 2H), 4.21 (t, J=5 Hz, 2H), 3.81 (t, J=5 Hz, 2H), 1.26 (m, 2H).

1. stirringThe mixture was stirred at room temperature for 12 hours
2. customquenched with methanol
3. filtrationfiltered through Celite
4. dissolutionThe filtrate was dissolved in diethyl ether (500 ml)
5. washwashed with water (3×200 ml)
6. customdried over Na2 SO4
7. concentrationThe ether layer was concentrated

ORD record

ord-2c7c15b5cf3e4b9785dd0e221cf8d7b8

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06436939B2