Acetone → 5-(2,4,6-Trimethylphenyl)-4-hydroxycyclopent-2-enone

HRID 407843Notes

Reaction equation

HRID 407843 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:10]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)O.CC(C)=[O:19]>O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[CH:10]1[C:12](=[O:19])[CH:16]=[CH:15][CH:14]1[OH:13]

Participants

4

Reactant 2

HCID 180AcetoneHCID 49962474(2,4,6-Trimethylphenyl)furan-2-ylmethanol

Product 1

HCID 666840085-(2,4,6-Trimethylphenyl)-4-hydroxycyclopent-2-enone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A solution of (2,4,6-trimethylphenyl)furan-2-ylmethanol (27.8 g, 129 mmol) in acetone (730 ml) and water (100 ml) is heated to 55° C. and polyphosphoric acid (2 g) is added. The mixture is stirred at 55° C. for 7 hours, then cooled to room temperature overnight. The reaction mixture is concentrated under reduced pressure to remove most of the acetone then ethyl acetate (500 ml) is added, and the reaction mixture is partitioned. The aqueous phase is extracted into ethyl acetate and the organic solutions are combined, washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give 5-(2,4,6-trimethylphenyl)-4-hydroxycyclopent-2-enone.

Workup

  1. temperaturecooled to room temperature overnight
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customto remove most of the acetone
  4. additionethyl acetate (500 ml) is added
  5. customthe reaction mixture is partitioned
  6. extractionThe aqueous phase is extracted into ethyl acetate
  7. washwashed with saturated aqueous sodium bicarbonate solution and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-03a80a937a0041a3a44d7c9afb53b33b
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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