Sodium Hydroxide → 2-(2-Chloro-2-propenyl)-5-(4-chlorobenzyl)-2-methylcyclopentanone

HRID 2283162Notes

Reaction equation

HRID 2283162 reaction equation
COC([C:5]1([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:9][CH2:8][C:7]([CH2:11][C:12]([Cl:14])=[CH2:13])([CH3:10])[C:6]1=[O:15])=O.[OH-].[Na+]>CC(O)C.O>[Cl:14][C:12](=[CH2:13])[CH2:11][C:7]1([CH3:10])[CH2:8][CH2:9][CH:5]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:6]1=[O:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86670684HCID 86670684, compound2×

Product 1

HCID 866706832-(2-Chloro-2-propenyl)-5-(4-chlorobenzyl)-2-methylcyclopentanone

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

3-(2-Chloro-2-propenyl)-1-(4-chlorobenzyl)-3-methyl-2-oxocyclopentane carboxylic acid methyl ester (Compound (XIII), R1=(Rb)Xbnb=CH2CCl═CH2, R2═CH3) (2.90 g, 8.16 mmol) was dissolved in i-PrOH (5 ml), and then an aqueous solution of NaOH (0.65 g, 16.3 mmol) dissolved in water (5.4 ml) was added, and stirring under reflux was conducted for 2.5 hours. Water (50 ml) was added, and extraction with hexane (50 ml×2) was conducted. The organic layer was dried over anhydrous sodium sulfate, and concentrated to obtain the desired substance

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. extractionextraction with hexane (50 ml×2)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain the desired substance

Sources & evidence

ORD record
ord-40650e4fe9094dfd9cee22e1e8f76c52
Source dataset
uspto-grants-2015_09
Patent number
US09145351B2

Reaction notes

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