tert-Butanol → HCID 11746277, compound

HRID 2041974Notes

Reaction equation

HRID 2041974 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](O)([CH3:12])([CH3:11])[CH3:10]>S(=O)(=O)(O)O>[C:9]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:5]=1[OH:8])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 97324-Fluorophenol

Product 1

HCID 11746277HCID 11746277, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Concentrated sulfuric acid (30 mL) was added to 4-fluorophenol (50 g, 446 mmol) and tert-butanol (60 g, 810 mmol), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was partitioned between hexane and water, and the hexane layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane) to give the title compound (6.8 g, 7%) as a colorless oil.

Workup

  1. customThe reaction mixture was partitioned between hexane and water
  2. washthe hexane layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-db23d170cc2c4c37a8bfef0491a26d8b
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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