Hydrochloric Acid → 2-Methyl-5-(4-chlorobenzylidene)-cyclopentanone

HRID 440568Notes

Reaction equation

HRID 440568 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([CH:8]=[C:9]2[CH2:13][CH2:12][C:11](C)([C:14](OC)=O)[C:10]2=[O:19])=[CH:6][CH:5]=1.Cl>O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[C:9]2[CH2:13][CH2:12][CH:11]([CH3:14])[C:10]2=[O:19])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67742476Methyl 3-(4-chlorobenzylidene)-1-methyl-2-oxocylopentanecarboxylate

Product 1

HCID 537529512-Methyl-5-(4-chlorobenzylidene)-cyclopentanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 12 g of sodium hydroxide in 20 ml of water was added to 10 g of methyl 3-(4-chloro-benzylidene)-1-methyl-2-oxocylopentanecarboxylate (I-1) (prepared in Example 1). The mixture was stirred for 2 hours at 80° C. The reaction mixture was poured into 10% aqueous solution of hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 4.1 g of an oily matter (yield, 51.8%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customto obtain
  6. custom4.1 g of an oily matter (yield, 51.8%)

Sources & evidence

ORD record
ord-23395d6cb26a41428953a5a61b9eee6c
Source dataset
uspto-grants-1996_05
Patent number
US05519160

Reaction notes

Loading…