Potassium Hydroxide → (Biphenyl-2-ylmethyl)propanedioic acid

HRID 444239Notes

Reaction equation

HRID 444239 reaction equation
[C:1]1([C:7]2[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=2[CH2:9][CH:10]([C:16]([O:18]CC)=[O:17])[C:11]([O:13]CC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>O.C(O)C>[C:1]1([C:7]2[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=2[CH2:9][CH:10]([C:16]([OH:18])=[O:17])[C:11]([OH:13])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12942384Diethyl [([1,1'-biphenyl]-2-yl)methyl]propanedioate

Product 1

HCID 261865(Biphenyl-2-ylmethyl)propanedioic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 149.0 g (0.456 mole) of diethyl (2-phenylbenzyl)malonate and 56.1 g (1.0 mole) of potassium hydroxide in 50 ml of water and 500 ml of ethanol was heated under reflux for 3 hours. The reaction mixture was allowed to cool to ambient temperature and stand for 60 hours. The ethanol was removed by distillation and the residue slurried in 400 ml of water. The mixture was extracted with one portion of 250 ml of diethyl ether. The aqueous phase was separated and acidified with concentrated hydrochloric acid, then extracted with two portions of 250 ml each of diethyl ether. The two extracts of the acidified aqueous phase were combined, dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give (2-phenylbenzyl)malonic acid as a pale yellow oil. The oil was used directly in the next step of this reaction sequence.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe ethanol was removed by distillation
  3. extractionThe mixture was extracted with one portion of 250 ml of diethyl ether
  4. customThe aqueous phase was separated
  5. extractionextracted with two portions of 250 ml each of diethyl ether
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-d2b991cb2e2d4cf1b96bfde080c18385
Source dataset
uspto-grants-1981_04
Patent number
US04263319

Reaction notes

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