Water → 2-Isopropyl-3-methoxyphenol

HRID 2266136Notes

Reaction equation

HRID 2266136 reaction equation
O[C:2]([C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1[OH:13])([CH3:4])[CH3:3].O.C([O-])=O.[NH4+]>C(O)(=O)C.[Pd]>[CH:2]([C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1[OH:13])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 595986452-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenol

Product 1

HCID 144655792-Isopropyl-3-methoxyphenolYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenol dissolved in acetic acid (50 mL) was added 10% palladium on charcoal (500 mg), water (6 mL), and ammonium formate (7.82 g, 124 mmol). After refluxing for 1 hour, the reaction was cooled and filtered through celite. The celite pad was washed with ethyl acetate (500 mL). Water (300 mL) was added to the filtrate, and the mixture was basified (pH=8) using solid sodium bicarbonate. The ethyl acetate layer was collected and washed with water, brine, dried using anhydrous sodium sulfate and concentrated to yield 2-Isopropyl-3-methoxy-phenol (3.68 g, 92%) as pale yellow solid.

Workup

  1. temperatureAfter refluxing for 1 hour
  2. temperaturethe reaction was cooled
  3. filtrationfiltered through celite
  4. washThe celite pad was washed with ethyl acetate (500 mL)
  5. additionWater (300 mL) was added to the filtrate
  6. customThe ethyl acetate layer was collected
  7. washwashed with water, brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-923cdce632804c29b39bcbc6d5e365e5
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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