Tert-butyl 4-tert-butyl-3-(cyclopropylmethoxy)phenyl carbonate → 4-tert-Butyl-3-(cyclopropylmethoxy)phenol

HRID 1350867Notes

Reaction equation

HRID 1350867 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][CH:20]2[CH2:22][CH2:21]2)[CH:9]=1)OC(C)(C)C>O1CCOCC1>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][C:10]=1[O:18][CH2:19][CH:20]1[CH2:21][CH2:22]1)([CH3:17])([CH3:15])[CH3:16]

Participants

3

Reactant 1

HCID 21097538Tert-butyl 4-tert-butyl-3-(cyclopropylmethoxy)phenyl carbonate

Product 1

HCID 210974984-tert-Butyl-3-(cyclopropylmethoxy)phenolYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a dioxane (10 mL) solution of tert-butyl 4-tert-butyl-3-(cyclopropylmethoxy)phenyl carbonate. (1.42 g, 4.43 mmol) was added 2M hydrochrolic acid (12 ml) at ambient temperature. The stirred mixture was refluxed for 18 hours. The reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate and then crude products were extracted with ethyl acetate. The organic layer was then washed with brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with hexane and ethyl acetate (9/1) to furnish 0.44 g (46% yield) of the title compound as a white solid.

Workup

  1. temperatureThe stirred mixture was refluxed for 18 hours
  2. customThe reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate
  3. extractioncrude products were extracted with ethyl acetate
  4. washThe organic layer was then washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customto separate solvent and sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto give a residue, which
  10. washeluted with hexane and ethyl acetate (9/1)

Sources & evidence

ORD record
ord-a103089bcd594c8c9a3478c0c8db36fe
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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