Sodium Hydroxide → 2-Cyclopropyl-6-methylphenol

HRID 1866838Notes

Reaction equation

HRID 1866838 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.[OH-].[Na+]>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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 119598072-Cyclopropyl-6-methylphenyl acetate

Product 1

HCID 229399512-Cyclopropyl-6-methylphenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A magnetic stirrer bar was attached to a 1 L round bottom flask. 2-Cyclopropyl-6-methylphenyl acetate (32.5 g), methanol (90 ml) and an aqueous 4M NaOH solution (90 ml) were added thereto, and the mixture was stirred at room temperature for 2 hours. After most of methanol was removed by concentration, the obtained mixture was cooled in ice-water and water (500 ml) and 4M hydrochloric acid (120 ml) were added thereto, followed by stirring of the mixture. 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 (3×200 ml) and a saturated aqueous NaCl solution (200 ml), followed by drying with anhydrous sodium sulfate. After the solid was removed by filtration, the filtrate was concentrated to obtain 27.09 g (purity: 54.6%) of a crude product of 2-cyclopropyl-6-methylphenol.

Workup

  1. customA magnetic stirrer bar was attached to a 1 L round bottom flask
  2. customAfter most of methanol was removed by concentration
  3. temperaturethe obtained mixture was cooled in ice-water
  4. additionwater (500 ml) and 4M hydrochloric acid (120 ml) were added
  5. stirringby stirring of the mixture
  6. extractionThis was extracted with a 10% ethyl acetate-90% hexane (V/V) solvent mixture (3×200 ml)
  7. washsuccessively washed with water (3×200 ml)
  8. dry with materialby drying with anhydrous sodium sulfate
  9. customAfter the solid was removed by filtration
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-22f4cdf6bf2d48ec994229774d52ca3e
Source dataset
uspto-grants-2009_12
Patent number
US07629494B2

Reaction notes

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