Ammonium Acetate → Methyl 2-(4-hydroxyphenyl)cyclopropane-1-carboxylate

HRID 1691523Notes

Reaction equation

HRID 1691523 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH:12]2[C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1)(=O)C.C([O-])(=O)C.[NH4+]>CO.O>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:13][CH:12]2[C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 59364054Methyl 2-[4-(acetyloxy)phenyl]cyclopropane-1-carboxylate

Product 1

HCID 59364069Methyl 2-(4-hydroxyphenyl)cyclopropane-1-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-[4-(acetyloxy)phenyl]cyclopropanecarboxylate (2.26 g, 9.65 mmol) was dissolved in a mixed solvent of methanol (80 mL) and water (20 mL), and ammonium acetate (5.95 g, 77.2 mmol) was added. The mixture was stirred at room temperature for 10 hr and further stirred at 60° C. for 8 hr. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60) to give the title compound (1.78 g, yield 96%) as colorless crystals.

Workup

  1. additionwas added
  2. stirringfurther stirred at 60° C. for 8 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60)

Sources & evidence

ORD record
ord-673af29b4c074b67b40a7c6db9c941bc
Source dataset
uspto-grants-2012_04
Patent number
US08153694B2

Reaction notes

Loading…