Hydrochloric Acid → HCID 66759828, compound

HRID 1402847Notes

Reaction equation

HRID 1402847 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:28])[CH2:9][CH:10]([CH:17]([C:23]([O:25]CC)=[O:24])[C:18]([O:20]CC)=[O:19])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:28])[CH2:9][CH:10]([CH:17]([C:23]([OH:25])=[O:24])[C:18]([OH:20])=[O:19])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66759220HCID 66759220, compound

Product 1

HCID 66759828HCID 66759828, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The solution of diethyl 2-[3-(4-chlorophenyl)-3-oxo-1-phenylpropyl]malonate (0.9 g) and 3M NaOH (7.5 ml) in ethanol (30 ml) was heated to reflux for 4 h. The mixture was cooled to rt, poured into water (30 ml), and acidified with 10% HCl. The aqueous layer was extracted three times with ethyl acetate (20 ml) and the combined organic layers were washed with brine and dried (magnesium sulfate). After evaporation of the solvent the residue was recrystallised from benzene to give 2-[3-(4-chlorophenyl)-3-oxo-1-phenylpropyl]malonic acid (0.5 g) as colourless solid.

Workup

  1. temperatureto reflux for 4 h
  2. extractionThe aqueous layer was extracted three times with ethyl acetate (20 ml)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. customAfter evaporation of the solvent the residue
  6. customwas recrystallised from benzene

Sources & evidence

ORD record
ord-c8f444978e224026b6b8bccf3fecc5fe
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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