Ammonium formate → 4-Methoxy-2-(propan-2-yl)phenol

HRID 38363

Reaction equation

HRID 38363 reaction equation
O[C:2]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[OH:13])([CH3:4])[CH3:3].C([O-])=O.[NH4+]>CC(O)=O.O.[Pd]>[CH:2]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[OH:13])([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 252417532-(2-Hydroxypropan-2-YL)-4-methoxyphenol

Product 1

HCID 183649974-Methoxy-2-(propan-2-yl)phenolYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-phenol (50.57 g, 278 mmol) in 550 ml AcOH was added 10% Pd/C (as a slurry in 20 ml H2O). Ammonium formate (87.52 g, 1388 mmol) was added in portions. The mixture was warmed to 100° C. for 1 hour, cooled and filtered through a pad of celite. The celite pad was washed with ethyl acetate. The mother liquor was mixed with H2O and extracted with ethyl acetate. The combined organics were washed with H2O, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give 2-isopropyl-4-methoxy-phenol (44.74 g, 97%) as a pale yellow oil.

Workup

  1. temperaturecooled
  2. filtrationfiltered through a pad of celite
  3. washThe celite pad was washed with ethyl acetate
  4. additionThe mother liquor was mixed with H2O
  5. extractionextracted with ethyl acetate
  6. washThe combined organics were washed with H2O
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3eedd24e572d4ffd938deda1333a9efc
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Linked notes

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