Water → 2-Cyclopropyl-6-methylphenol

HRID 1866825Notes

Reaction equation

HRID 1866825 reaction equation
C([O:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:12]1[CH2:14][CH2:13]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH:12]1([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=2[OH:4])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 119598072-Cyclopropyl-6-methylphenyl acetate

Product 1

HCID 229399512-Cyclopropyl-6-methylphenolYield 67.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 ml three-necked round-bottomed flask was equipped with a magnetic stirrer bar, a thermometer and a drying tube. A solution of 2-cyclopropyl-6-methylphenyl acetate (18.3 g, 96.2 mmol) in methanol (100 ml) was added thereto. Potassium carbonate (26.5 g, 192 mmol) was added thereto at once and the mixture was stirred at room temperature for 75 minutes. After water (300 ml) was added to the reaction mixture, the resulting mixture was concentrated by an evaporator to remove most of methanol. The obtained mixture was cooled to 0° C. and 4M hydrochloric acid (100 ml) was added thereto such that the temperature of the mixture did not exceed 25° C. This was extracted with a 10% ethyl acetate-90% hexane (V/V) solvent mixture (3×200 ml). The organic layer was combined and successively washed with water (2×200 ml) and a saturated aqueous NaCl solution (50 ml), followed by drying with anhydrous sodium sulfate (90 g). After the solid was removed by filtration and the filtrate was concentrated to obtain 13.8 g of a crude product of 2-cyclopropyl-6-methylphenol as a brown oil. The crude product was distilled (7.6-7.8 mmHg, 94-98° C.) to obtain 9.64 g of 2-cyclopropyl-6-methylphenol as a light purple oil.

Workup

  1. customA 500 ml three-necked round-bottomed flask was equipped with a magnetic stirrer bar
  2. concentrationthe resulting mixture was concentrated by an evaporator
  3. customto remove most of methanol
  4. temperatureThe obtained mixture was cooled to 0° C.
  5. addition4M hydrochloric acid (100 ml) was added
  6. customdid not exceed 25° C
  7. extractionThis was extracted with a 10% ethyl acetate-90% hexane (V/V) solvent mixture (3×200 ml)
  8. washsuccessively washed with water (2×200 ml)
  9. dry with materialby drying with anhydrous sodium sulfate (90 g)
  10. customAfter the solid was removed by filtration
  11. concentrationthe filtrate was concentrated
  12. customto obtain 13.8 g of a crude product of 2-cyclopropyl-6-methylphenol as a brown oil
  13. distillationThe crude product was distilled (7.6-7.8 mmHg, 94-98° C.)

Sources & evidence

ORD record
ord-04ceda2100c34470afc105ecb9d46e19
Source dataset
uspto-grants-2009_12
Patent number
US07629494B2

Reaction notes

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