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

HRID 1860659Notes

Reaction equation

HRID 1860659 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 1 N HCl solution. The mixture was stirred for 15 min and filtered through a short column of Celite®. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried with MgSO4, and concentrated to give an 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 1 N HCl solution
  2. stirringThe mixture was stirred for 15 min
  3. filtrationfiltered through a short column of Celite®
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried with MgSO4
  6. concentrationconcentrated
  7. customto give an oil in 11.6 g
  8. customThis product was used without further purification

Sources & evidence

ORD record
ord-f33c24492b35433ab625dc48cb19cbeb
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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