Potassium Hydroxide → HCID 12740769, compound

HRID 1612881Notes

Reaction equation

HRID 1612881 reaction equation
[CH2:1]([C:8]([C:21]#[N:22])([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]([O:11]CC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>O.C(O)C.O>[CH2:14]([C:8]([C:21]#[N:22])([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([OH:11])=[O:10])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 11044573HCID 11044573, compound

Product 1

HCID 12740769HCID 12740769, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

Ethyl 2-benzyl-2-cyano-3-phenylpropionate (3.20 g, 11 mmol) was saponified at room temperature overnight with potassium hydroxide (6.17 g, 0.11 mol) in 10% water/ethanol. The mixture was diluted with water (200 mL) and extracted with hexane (2×50 mL). The aqueous layer was acidified with 1M phosphoric acid and extracted with methylene chloride (4×100 mL). The combined organic extracts were dried over magnesium sulfate and freed of solvent to afford 2-benzyl-2-cyano-3-phenylpropionic acid (2.94 g, 11 mmol) as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 7.34 (br s, 10 H), 3.24 (dd, J=13.5, 57 Hz); mass spectrum m/e 283 (M+NH4+).

Workup

  1. extractionextracted with hexane (2×50 mL)
  2. extractionextracted with methylene chloride (4×100 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate

Sources & evidence

ORD record
ord-1a0424da5b634df880cda4efe63ecfd9
Source dataset
uspto-grants-1993_03
Patent number
US05190922

Reaction notes

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