Oxygen → 4-Fluoro-2-(hydroxymethyl)phenol

HRID 1913788Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].O=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C1COCC1.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH2:7][OH:8])[CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

27.1 g (159.28 mmol) of methyl 5-fluoro-2-hydroxybenzoate are introduced into 500 ml of dry THF with exclusion of oxygen and cooled to 0° C. Subsequently, while cooling, 238 ml (238 mmol) of a 1 M solution of lithium aluminium hydride in THF are slowly added dropwise, and the mixture is stirred at 0° C. for 1 hour and then at RT overnight. After reaction is complete, saturated ammonium chloride solution is added to the mixture, and it is taken up in dichloromethane. The organic phase is separated off and dried over sodium sulphate. After filtration, the solvent is removed in vacuo. The crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1). 18.0 g (126.6 mmol, 79% of theory) of a colourless solid are isolated.

Workup

temperatureSubsequently, while cooling
customat RT
customovernight
customAfter reaction
customThe organic phase is separated off
dry with materialdried over sodium sulphate
filtrationAfter filtration
customthe solvent is removed in vacuo
customThe crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1)
custom18.0 g (126.6 mmol, 79% of theory) of a colourless solid are isolated

Sources & evidence

ORD record: ord-92c4256f51474819b3d6cd5c9780e54f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609727B2

Reaction notes

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