4-Chloro-3-methoxybenzoic acid → (4-Chloro-3-methoxyphenyl)methanol

A solution of 4-chloro-3-methoxybenzoic acid (1.12 g, 5.98 mmol) in THF (30 mL) was stirred on an ice bath and treated with a 1.0 M tetrahydrofuran solution of lithium aluminum hydride (7.18 mL, 7.18 mmol) over about a 5 min. period. The solution was stirred on ice for 2 h, and then quenched with rapid stirring by the slow dropwise addition of water (0.27 mL), followed by 15% aqueous sodium hydroxide (0.27 mL), then water (0.82 mL) again. Upon completion of addition, the resulting suspension was filtered and the collected solid was washed with ethyl acetate. The filtrate was concentrated under vacuum to provide (4-chloro-3-methoxyphenyl)methanol as a colorless oil (737 mg, 71%). 1H NMR (400 MHz, CDCl3) δ ppm 3.92 (s, 3 H) 4.67 (s, 2 H) 6.87 (d, J=7.6 Hz, 1 H) 6.98 (s, 1 H) 7.33 (d, J=7.6 Hz, 1 H).

1. customquenched
2. stirringwith rapid stirring by the slow dropwise addition of water (0.27 mL)
3. additionUpon completion of addition
4. filtrationthe resulting suspension was filtered
5. washthe collected solid was washed with ethyl acetate
6. concentrationThe filtrate was concentrated under vacuum

ORD record

ord-dd2ae8a627d2434790ee8b054c2fbd75

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759390B2