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

HRID 1752016Notes

Reaction equation

HRID 1752016 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=CH3, (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-666d3de539ce4282ab114aca2ffd7d0e
Source dataset
uspto-grants-2015_10
Patent number
US09162966B2

Reaction notes

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