Acetone → 5-(5-Bromo-2-ethylphenyl)-4-hydroxycyclopent-2-enone

HRID 407850Notes

Reaction equation

HRID 407850 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH3:16])=[C:6]([CH:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)O)[CH:7]=1.CC(C)=[O:19]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH3:16])=[C:6]([CH:8]2[C:12](=[O:11])[CH:13]=[CH:14][CH:10]2[OH:19])[CH:7]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 58061495(5-Bromo-2-ethylphenyl)furan-2-ylmethanol

Product 1

HCID 580615165-(5-Bromo-2-ethylphenyl)-4-hydroxycyclopent-2-enone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A solution of (5-bromo-2-ethylphenyl)furan-2-ylmethanol (40.73 g, 0.145 mol) in acetone (1150 ml) and water (170 ml) is heated to 55° C. and 30 drops of polyphosphoric acid are added. The mixture is stirred at 55° C. for 44 hours, then cooled to room temperature. 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-(5-bromo-2-ethylphenyl)-4-hydroxycyclopent-2-enone.

Workup

  1. temperaturecooled to room temperature
  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-7ee75005eb3a4533bb975eaa248cec88
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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