Sodium Hydroxide → HCID 18980811, compound

HRID 2392952Notes

Reaction equation

HRID 2392952 reaction equation
[C:1]1([CH:7]([CH:9]([C:15]([O-:17])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CC(C)=O.O>[CH2:13]([O:12][C:10]([CH:9]([CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:8])[C:15]([OH:17])=[O:16])=[O:11])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86169512Ethyl (1-phenylethyl)malonate

Product 1

HCID 18980811HCID 18980811, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

The ethyl (1-phenylethyl)malonate is stirred overnight with sodium hydroxide (1.3 eq) in an acetone/water (3:1 by volume) mixture. After concentrating to dryness, the residue is taken up with water (40 mL) and the mixture is then extracted three times with ethyl acetate (25 mL). The organic phase is washed, dried, filtered and concentrated to dryness to yield 3.5 g of 2-ethoxycarbonyl-3-phenylbutanoic acid in a 65% yield in the form of an oil, having the following characteristics: Rf =0.50 [methylene chloride/methanol (9:1 by volume)].

Workup

  1. concentrationAfter concentrating to dryness
  2. extractionthe mixture is then extracted three times with ethyl acetate (25 mL)
  3. washThe organic phase is washed
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-476cdb3092a24be1ba531b1c33d5755a
Source dataset
uspto-grants-1998_09
Patent number
US05801274

Reaction notes

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