Reaction #66670

Reaction equation

water

ammonium formate

2-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenol

→

2-Isopropyl-3-methoxy-phenol

Yield 92.0%

Solvents

acetic acid

Conditions

Workup

1. 1
   TemperatureAfter refluxing for 1 hour
2. 2
   Temperaturethe reaction was cooled
3. 3
   Filtrationfiltered through celite
4. 4
   WashThe celite pad was washed with ethyl acetate (500 mL)
5. 5
   workup.ADDITIONWater (300 mL) was added to the filtrate
6. 6
   OtherThe ethyl acetate layer was collected
7. 7
   Washwashed with water, brine
8. 8
   Otherdried
9. 9
   Concentrationconcentrated

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.

Source