Trifluoroacetic acid → 4-tert-Butyl-3-(2-methoxyethoxy)phenol

HRID 1350862Notes

Reaction equation

HRID 1350862 reaction equation
C(=O)([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])[CH:9]=1)OC(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][C:10]=1[O:18][CH2:19][CH2:20][O:21][CH3:22])([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21097537tert-Butyl 4-tert-butyl-3-(2-methoxyethoxy)phenyl carbonate

Product 1

HCID 210974934-tert-Butyl-3-(2-methoxyethoxy)phenolYield 59.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene dichloride (3 ml) solution of tert-butyl 4-tert-butyl-3-(2-methoxyethoxy)phenyl carbonate (792 mg, 2.4 mmol) was added trifluoroacetic acid (TFA) (3 ml) and the mixture was stirred for 1 hour at ambient temperature. The solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane=⅓ to furnish 0.32 g (59% yield) of the title compound as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give a residue, which
  3. washeluted with ethyl acetate/hexane=⅓

Sources & evidence

ORD record
ord-b21c5f9208ff468dae39e6e4a163b1d5
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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