3-Chloro-4-fluorobenzoic acid → 3-Chloro-4-fluorobenzyl alcohol

HRID 1034302Notes

Reaction equation

HRID 1034302 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[F:17])[C:11](O)=[O:12]>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[F:17])[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 5209893-Chloro-4-fluorobenzoic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 27736073-Chloro-4-fluorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of LiAlH4 (2.2 g) in THF (100 mL) at 0° C. under nitrogen was added 3-chloro-4-fluorobenzoic acid (Aldrich; 10 g). After stirring for 1 hour at 0° C. the mixture was stirred for 1 hour at 25° C. followed by the addition of a further 1.0 g of LiAlH4. Stirring was continued for a further 12 hours at 25° C. after which time the mixture was cooled to 0° C. and quenched with H2O. The mixture was then acidified with 1N HCl (aq) and extracted with EtOAc. After washing with NaHCO3 (aq) and drying (MgSO4), the organic solution was evaporated to give the title compound as an oil.

Workup

  1. stirringwas stirred for 1 hour at 25° C.
  2. stirringStirring
  3. waitwas continued for a further 12 hours at 25° C.
  4. temperatureafter which time the mixture was cooled to 0° C.
  5. customquenched with H2O
  6. extractionextracted with EtOAc
  7. washAfter washing with NaHCO3 (aq)
  8. dry with materialdrying (MgSO4)
  9. customthe organic solution was evaporated

Sources & evidence

ORD record
ord-5ebbb7b3d22f4ff2bd72bd263922e686
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

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