Acetic Acid → 4-cyclopropanecarbonylphenol

HRID 1057772Notes

Reaction equation

HRID 1057772 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

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) resulting in the formation of a yellow precipitate. After refluxing for 60 minutes, water (50 mL) was added and the resulting mixture was refluxed for another 60 minutes, allowed to cool to ambient 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 residue was crystallized from chloroform/hexanes to provide 26.65 g (95%) of the title compound. MS (APCI(−)) m/z 161 (M-H)−; 1H NMR (300 MHz, CDCl3) δ 7.9 (d, 2H), 6.9 (d, 2H), 2.65 (m, 1H), 1.23 (m, 2H), 1.03 (m, 2H).

Workup

  1. customresulting in the formation of a yellow precipitate
  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 residue was crystallized from chloroform/hexanes

Sources & evidence

ORD record
ord-a4f142e116114ddb9041a9a74952a074
Source dataset
uspto-grants-2003_02
Patent number
US06515013B2

Reaction notes

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