Tetrahydrofuran → (3-Fluoro-4-methylphenyl)methanol

HRID 1860650Notes

Reaction equation

HRID 1860650 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1OC)[CH:5]=[O:6].[H-].[CH2:13]1COCC1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[CH3:13]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 676963-Fluoro-p-anisaldehydeHCID 166653Hydride

Product 1

HCID 2774590(3-Fluoro-4-methylphenyl)methanol

Procedure

3-fluoro-p-anisaldehyde (12.5 g, 81.1 mmol) was dissolved in 100 ml THF. Under N2 a solution of diisobutylalumium hydride (100 ml, 1M in THF) was added at 0° C. over 30 min. The reaction was stirred for 30 min and quenched with 250 ml 1N HCl solution. The resulting mixture was stirred for 15 min and filtered through a short column of Celite®. The product was extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried with MgSO4, and concentrated to give a viscous oil in 11.6 g. This product was used without further purification. NMR spectra of the product were consistent for the proposed structure.

Workup

  1. customquenched with 250 ml 1N HCl solution
  2. stirringThe resulting mixture was stirred for 15 min
  3. filtrationfiltered through a short column of Celite®
  4. extractionThe product was extracted with ethyl acetate
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layer was dried with MgSO4
  7. concentrationconcentrated
  8. customto give a viscous oil in 11.6 g
  9. customThis product was used without further purification

Sources & evidence

ORD record
ord-bf392f0a846f4d91a1843c480a0448e3
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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