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

HRID 1168090

Reaction equation

C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:7]([Cl:21])[CH:6]=1)C.[H-]>ClCCl>[Cl:11][C:9]1[CH:10]=[C:5]([CH2:4][OH:3])[CH:6]=[C:7]([Cl:21])[C:8]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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) δ7.39 (s, 2H), 6.74-6.82 (m, 4H), 4.69 (d, 2H), 3.76 (s, 3H), 1.83 (t, 1 H).

Workup

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

Sources & evidence

ORD record: ord-0133d51d904c4f07ad48b04650104254
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620830B2

Linked notes

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