Water → (4,5-Dichloro-2-methoxyphenyl)methanol

HRID 588828Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[C:17]([Cl:18])=[CH:16][C:11]([C:12](OC)=[O:13])=[C:10]([O:19][CH3:20])[CH:9]=1.O.[OH-].[Na+]>C1COCC1>[Cl:7][C:8]1[C:17]([Cl:18])=[CH:16][C:11]([CH2:12][OH:13])=[C:10]([O:19][CH3:20])[CH:9]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a mixture of LiAlH4 (2.42 g, 64 mmol) in THF (40 mL) at −40° C. under argon, a solution of methyl 4,5-dichloro-2-methoxybenzoate (6 g, 26 mmol) in THF (50 mL) was added dropwise. The reaction mixture was stirred at −5° C. to 5° C. for 1 h. The mixture was cooled to −20° C. and then water (2 mL) and NaOH (15%) aqueous were added. The resulting mixture was stirred for 15 min. The solid was filtered, and the cake rinsed with ethyl acetate. The combined filtrate was dried over Na2SO4 and concentrated in vacuo to afford the crude product (4.6 g).

Workup

stirringThe resulting mixture was stirred for 15 min
filtrationThe solid was filtered
washthe cake rinsed with ethyl acetate
dry with materialThe combined filtrate was dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-14093d7cd0e14a45b06610b6363a47ca
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227978B2

Reaction notes

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