Acetone → HCID 58502815, compound

HRID 40471Notes

Reaction equation

HRID 40471 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:19][CH3:20])=[C:10]([CH:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)O)[CH:11]=2)=[CH:4][CH:3]=1.CC(C)=[O:25]>O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:19][CH3:20])=[C:10]([CH:12]3[C:16](=[O:15])[CH:17]=[CH:18][CH:14]3[OH:25])[CH:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 58502794(4'-Chloro-4-ethylbiphen-3-yl)furan-2-ylmethanol

Product 1

HCID 58502815HCID 58502815, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A solution of (4′-chloro-4-ethylbiphen-3-yl)furan-2-ylmethanol (67.18 g, 214.8 mmol) in acetone (1340 ml) and water (235 ml) is heated to 55° C. and 30 drops of polyphosphoric acid are added. The mixture is stirred at 55° C. for 25 hours, then cooled to room temperature. The reaction mixture is concentrated under reduced pressure to remove most of the acetone then ethyl acetate (600 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-(4′-chloro-4-ethylbiphen-3-yl)-4-hydroxy-cyclopent-2-enone (59.84 g) as a brown oil.

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 (600 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-19d4855be5024ea9a0f79a20a730ded4
Source dataset
uspto-grants-2013_09
Patent number
US08530388B2

Reaction notes

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