Sodium Hydroxide → Benzenepropanoic acid, alpha-(phenylmethyl)-

HRID 1607386Notes

Reaction equation

HRID 1607386 reaction equation
C([O:3][C:4](=[O:20])[CH:5]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH2:13]([CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:20])=[O:3])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 249277Ethyl 2-benzyl-3-phenylpropanoate

Product 1

HCID 64800Benzenepropanoic acid, alpha-(phenylmethyl)-Yield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3.4 g of 2-benzyl-3-phenylpropionic acid ethyl ester in 170 ml of ethanol was added 34 ml of a 2N-aqueous sodium hydroxide solution, and the mixture was heated under reflux for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was washed with diethyl ether to remove neutral materials, then the aqueous solution was acidified by adding concentrated hydrochloric acid. The aqueous solution was extracted with diethyl ether. The ethereal layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 2.8 g of 2-benzyl-3-phenylpropionic acid as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. washThe mixture was washed with diethyl ether
  6. customto remove neutral materials
  7. additionby adding concentrated hydrochloric acid
  8. extractionThe aqueous solution was extracted with diethyl ether
  9. washThe ethereal layer was washed with a saturated sodium chloride aqueous solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c9ddaa9b82aa4ecbbc050697571a4677
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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