Potassium Hydroxide → 3-Phenyl-2-t-butylcarboxymethylpropionic acid

HRID 260652Notes

Reaction equation

HRID 260652 reaction equation
[C:1]1([CH2:7][C:8]([CH2:18][C:19]([OH:21])=[O:20])([C:14]([CH3:17])([CH3:16])[CH3:15])[C:9]([O:11]CC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>C(O)C.O>[C:1]1([CH2:7][C:8]([CH2:18][C:19]([OH:21])=[O:20])([C:14]([CH3:15])([CH3:16])[CH3:17])[C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 867490123-Phenyl-2-t-butylcarboxymethylpropionic acid, ethyl ester

Product 1

HCID 542707623-Phenyl-2-t-butylcarboxymethylpropionic acidYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Dissolve 3-phenyl-2-t-butylcarboxymethylpropionic acid, ethyl ester (2.68 g, 9.17 mmol) in ethanol (95%, 60 mL) and water (30 mL). Treat with potassium hydroxide (2.94 g, 52 mmol). Stir at room temperature for 3 hours. Add water (75 mL) and extract with ethyl ether (2×50 mL). Extract the combined ethereal phases with water (75 mL) and acidify the combined aqueous phases with aqueous 1M tartaric acid (pH 2-3). Extract with ethyl acetate (2×125 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Take the residue up in methylene chloride and filter to give 3-phenyl-2-t-butylcarboxymethylpropionic acid as a pale yellow solid (1.96 g, 81%).

Workup

  1. extractionAdd water (75 mL) and extract with ethyl ether (2×50 mL)
  2. extractionExtract the combined ethereal phases with water (75 mL)
  3. extractionExtract with ethyl acetate (2×125 mL)
  4. dry with materialdry (Na2SO4)
  5. customevaporate the solvent in vacuo
  6. filtrationfilter

Sources & evidence

ORD record
ord-33754768f1eb40528bce0d78b0b73a8d
Source dataset
uspto-grants-1996_06
Patent number
US05529997

Reaction notes

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