Water → (2,3,4,5-Tetrafluoro-6-methylphenyl)methanol

HRID 2296508Notes

Reaction equation

HRID 2296508 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([CH3:11])[C:3]=1[C:12](O)=[O:13].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH3:11][C:4]1[C:5]([F:10])=[C:6]([F:9])[C:7]([F:8])=[C:2]([F:1])[C:3]=1[CH2:12][OH:13]

Participants

5

Reactant 3

HCID 962WaterHCID 129439972,3,4,5-Tetrafluoro-6-methylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 12943998(2,3,4,5-Tetrafluoro-6-methylphenyl)methanolYield 42.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3,4,5,6-tetrafluoro-2-toluic acid (500 mg) was dissolved in dry diethyl ether (5.0 ml) added dropwise to a suspension of lithium aluminium hydride (100 mg) in dry ether (10 ml) under an argon atmosphere at the ambient temperature. When the addition was complete and the effervescence had subsided the mixture was heated at the reflux temperature for a period of 1 hour. After allowing the mixture to cool to the ambient temperature water (10 ml) was cautiously added and the resultant mixture extracted with diethyl ether (2×20 ml), the extracts washed with water and dried over anhydrous magnesium sulphate. After filtration the filtrate was concentrated by evaporation of the solvent. The residual low melting solid was recrystallised from petroleum ether (boiling range 40°-60° C.) to yield 2-methyl-3,4,5,6-tetrafluorobenzyl alcohol (200 mg). N.m.r. (1H(ppm)CDCl3): 2.18(s,1H); 2.32(t,3H); 4.86(s,2H).

Workup

  1. additionWhen the addition
  2. temperaturewas heated at the reflux temperature for a period of 1 hour
  3. additionwas cautiously added
  4. extractionthe resultant mixture extracted with diethyl ether (2×20 ml)
  5. washthe extracts washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationAfter filtration the filtrate
  8. concentrationwas concentrated by evaporation of the solvent
  9. customThe residual low melting solid was recrystallised from petroleum ether (boiling range 40°-60° C.)

Sources & evidence

ORD record
ord-8dd707192fe84f0fa6a4d0d93e2863ac
Source dataset
uspto-grants-1984_01
Patent number
US04429153

Reaction notes

Loading…