Acetic Acid → 4-cyclopropanecarbonylphenol

HRID 411248Notes

Reaction equation

HRID 411248 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:15])[CH2:11][CH2:12][CH2:13]Cl)=[CH:6][CH:5]=1.C(O)(=O)C>O>[CH:11]1([C:10]([C:7]2[CH:8]=[CH:9][C:4]([OH:3])=[CH:5][CH:6]=2)=[O:15])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium Hydroxide3×HCID 815784-Chloro-4'-hydroxybutyrophenone2×

Product 1

HCID 10515124-cyclopropanecarbonylphenolYield 119.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A refluxing solution of sodium hydroxide in water (50% (w/w), 40.4 mL) was treated over a period of 15 minutes with para-hydroxy-4-chlorobutyrophenone (25.0 g, 137 mmol), followed by additional aqueous sodium hydroxide (25% (w/w), 177 mL). Additional para-hydroxy-4-chlorobutyrophenone (25.0 g, 137 mmol) was added portionwise to the reaction mixture, followed by solid sodium hydroxide (40.4 g). A yellow precipitate formed. After refluxing for 60 minutes, water (50 mL) was added and the resulting mixture was refluxed for another 60 minutes, cooled to room temperature, diluted with water (100 mL) and neutralized with acetic acid. The precipitate was collected by filtration, washed with water, air-dried, and triturated at 40° C. with chloroform (1.5 L). The chloroform solution was dried (MgSO4), filtered, and concentrated. The concentrate was recrystallized from chloroform/hexanes to afford 26.65 g (95%) of the desired product.

Workup

  1. customA yellow precipitate formed
  2. temperatureAfter refluxing for 60 minutes
  3. temperaturethe resulting mixture was refluxed for another 60 minutes
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customair-dried
  7. customtriturated at 40° C. with chloroform (1.5 L)
  8. dry with materialThe chloroform solution was dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe concentrate was recrystallized from chloroform/hexanes

Sources & evidence

ORD record
ord-ee85432b0a7a48b88b569a992ad1cf7f
Source dataset
uspto-grants-2003_05
Patent number
US06559140B2

Reaction notes

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