Hydride → 3,5-Dichloro-4-(4-methoxyphenoxy)benzyl Alcohol

Temperature

0 °C

To a solution of 3,5-dichloro-4-(4-methoxy-phenoxy)-benzoic acid ethyl ester (1.36 g, 4.01 mmol) in dichloromethane (35 ml) at 0° C. was added diisobutylaluminun hydride (1M in toluene, 12 ml, 12 mmol) and the mixture was stirred for 2.5 hours at 0° C. The reaction mixture was quenched with potassium sodium tartrate tetrahydrate (0.5 M aqueous solution, 50 ml), stirred for 20 minutes at room temperature and then was filtered through diatomaceous earth. The filtrate was concentrated and then taken up in water (60 ml). The aqueous solution was extracted with ethyl acetate (4×60 ml). The combined extracts were dried, filtered, and concentrated. The residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane) to afford the title compound (871 mg). NMR (400 MHz, CDCl3) δ 7.39 (s, 2H), 6.74-6.82 (m, 4H), 4.69 (d, 2H), 3.76 (s, 3H), 1.83 (t, 1H).

1. customThe reaction mixture was quenched with potassium sodium tartrate tetrahydrate (0.5 M aqueous solution, 50 ml)
2. stirringstirred for 20 minutes at room temperature
3. filtrationwas filtered through diatomaceous earth
4. concentrationThe filtrate was concentrated
5. extractionThe aqueous solution was extracted with ethyl acetate (4×60 ml)
6. customThe combined extracts were dried
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane)

ORD record

ord-f791466981604033a7009e4b0706de32

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06960604B2