Tetrahydrofuran → 4-(1-Hydroxy-4-phenyl-2-butyl) anisole

HRID 1598626Notes

Reaction equation

HRID 1598626 reaction equation
[CH2:1]([Mg]Br)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:12]([CH2:19]C(=O)C)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C[O:26][CH2:25]C1>>[OH:26][CH2:25][CH:1]([C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[CH2:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 17355Benzyl acetoneHCID 178418276HCID 178418276, compound

Product 1

HCID 543717404-(1-Hydroxy-4-phenyl-2-butyl) anisole

Procedure

An 0.5M solution of 4-anisyl magnesium bromide in THF (66.7 mL. 33.3 mmol) was added dropwise to an ice-water cooled solution of benzyl acetone (5.0 mL, 33.3 mmol) in THF. The resulting reaction was allowed to warm to room temperature, and after 1h was partitioned between aqueous ammonium chloride and ether. The organic phase was dried over magnesium sulfate, concentrated, and purified by chromatography over silica gel eluted with 1:5 ethyl acetate/hexanes to afford 6.2 g of 4-(1-hydroxy-4-phenyl-2-butyl) anisole as a clear oil.

Workup

  1. customThe resulting reaction
  2. customafter 1h was partitioned between aqueous ammonium chloride and ether
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by chromatography over silica gel
  6. washeluted with 1:5 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bae015b464ed40928dd5ceff230107e4
Source dataset
uspto-grants-1998_04
Patent number
US05739140

Reaction notes

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