HCID 58502816, compound → 2-(4'-Chloro-4-ethylbiphen-3-yl)-1,3-cyclopentanedione

HRID 40469Notes

Reaction equation

HRID 40469 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:20][CH3:21])=[C:10]([C:12]3[C:13](=[O:19])[CH2:14][CH2:15][C:16]=3[O:17]C)[CH:11]=2)=[CH:4][CH:3]=1>CC(C)=O.Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:20][CH3:21])=[C:10]([CH:12]3[C:13](=[O:19])[CH2:14][CH2:15][C:16]3=[O:17])[CH:11]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 1

HCID 58502816HCID 58502816, compound

Product 1

HCID 468300792-(4'-Chloro-4-ethylbiphen-3-yl)-1,3-cyclopentanedione

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of 2-(4′-chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone (200 mg, 0.61 mmol) in acetone (4 ml) and 2M aqueous hydrochloric acid (4 ml) is heated at 120° C. for 20 minutes under microwave irradiation. The reaction mixture is diluted with water (20 ml) and 2M aqueous hydrochloric acid (10 ml), and the crude product is extracted with ethyl acetate (3×15 ml). The organic extracts are combined, washed with brine (10 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to dryness under reduced pressure to give 2-(4′-chloro-4-ethylbiphen-3-yl)-1,3-cyclopentanedione.

Workup

  1. extractionthe crude product is extracted with ethyl acetate (3×15 ml)
  2. washwashed with brine (10 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6f7641894d3b4895a473f13086f5e497
Source dataset
uspto-grants-2013_09
Patent number
US08530388B2

Reaction notes

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