Hydrochloric Acid → 2-Cyclobutylphenol

HRID 522262Notes

Reaction equation

HRID 522262 reaction equation
Cl.[CH:2]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:12]COC)[CH2:5][CH2:4][CH2:3]1.CCOC(C)=O>CO>[CH:2]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])[CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 681090621-Cyclobutyl-2-(methoxymethoxy)benzene

Product 1

HCID 128063072-CyclobutylphenolYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

After concentrated hydrochloric acid (3.1 mL) was added to a solution of 1-cyclobutyl-2-(methoxymethoxy)benzene (1.43 g) in MeOH (29 mL) at room temperature, the mixture was stirred at 60° C. for 2 hours. After the reaction mixture was cooled to room temperature, a standard buffer solution of pH 6.86 was added thereto, and EtOAc was added. Extraction was performed on the mixture using EtOAc, and the extract was washed with saturated brine. The organic layer was dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure, whereby 2-cyclobutylphenol (1.1 g) was obtained as a colorless oil.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. additiona standard buffer solution of pH 6.86 was added
  3. extractionExtraction
  4. washthe extract was washed with saturated brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-556b5063bf5544718de54f043c805c00
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

Loading…