2-Fluoro-5-methylbenzoic acid → (2-Fluoro-5-methylphenyl)methanol

HRID 1094448Notes

Reaction equation

HRID 1094448 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:9]=1[C:10](O)=[O:11]>C1COCC1.CCOCC>[F:7][C:8]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 2

HCID 2428292-Fluoro-5-methylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 12407611(2-Fluoro-5-methylphenyl)methanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 1M solution of lithium aluminum hydride in THF (57 mL) at 0° C. is added a solution of 2-fluoro-5-methylbenzoic acid (8.0 g, 52 mmol) in 160 mL of ether drop-wise. The reaction is then heated at reflux for 1.5 hr. The reaction is then cooled to 0° C. and is quenched with H2O (4 mL), aqueous 40% NaOH (4 mL) and H2O (4 mL). The resultant slurry is then filtered through celite and MgSO4. The filtrate is then concentrated and purified by silica gel flash column chromatography to provide the title compound.

Workup

  1. temperatureThe reaction is then heated
  2. temperatureat reflux for 1.5 hr
  3. customis quenched with H2O (4 mL), aqueous 40% NaOH (4 mL) and H2O (4 mL)
  4. filtrationThe resultant slurry is then filtered through celite and MgSO4
  5. concentrationThe filtrate is then concentrated
  6. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-d7b45df2691849d3932f816e216e1c1a
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

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