Water → (4-Fluoro-2-methylphenyl)methanol

HRID 749465Notes

Reaction equation

HRID 749465 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([CH3:11])[CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 187837944-Fluoro-2-methylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 3872017(4-Fluoro-2-methylphenyl)methanolYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Fluoro-2-methylbenzoate (15.3 g, 91 mmol) was dissolved in THF under a stream of nitrogen. The mixture was cooled to 0° C. while adding LiAlH4 (4.4 g, 110 mmol) in small portions and then stirred at room temperature for 1 h. Water (4.4 mL), aqueous 15% NaOH (4.4 mL) and then more water (13.2 mL) were added dropwise in the given order while cooling to 0° C. The mixture was stirred for 2 h and then the solid material was filtered off. The solvent was removed by evaporation and there was obtained 11.5 g (90%) of (4-fluoro-2-methylphenyl)methanol as an oil. 1H NMR (300 MHz, CDCl3): 2.4 (s, 3H), 4.6 (s, 2H), 6.8-6.9 (m, 2H), 7.3 (t, 1H).

Workup

  1. temperaturewhile cooling to 0° C
  2. stirringThe mixture was stirred for 2 h
  3. filtrationthe solid material was filtered off
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-2e6b73acf2ea440da913fa52e525255b
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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