Sodium Hydroxide → 4-Cyanophenylacetic acid

HRID 1372439Notes

Reaction equation

HRID 1372439 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12]C)=[O:11])=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+]>C(O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 1512619Methyl (4-cyanophenyl)acetate

Product 1

HCID 795874-Cyanophenylacetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 4-cyanophenylacetate (23.9 g; 0.136 mol) in ethanol (250 mL) was stirred at room temperature and a solution of sodium hydroxide (6.0 g; 0.15 mol) in water (25 mL) was added. After 2 hours the ethanol was removed in vacuo. Ethyl acetate (300 mL) and 5% aqueous HCl (300 mL) were added and the layers were separated. The aqueous layer was extracted with ethyl acetate (300 mL) and the combined organic layers were dried (MgSO4) and evaporated in vacuo to give the acid (21.6 g; 99%) which was used without further purification.

Workup

  1. customAfter 2 hours the ethanol was removed in vacuo
  2. additionEthyl acetate (300 mL) and 5% aqueous HCl (300 mL) were added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (300 mL)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. customevaporated in vacuo
  7. customto give the acid (21.6 g; 99%) which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-b54e95d73136444b8c258d0c154457c2
Source dataset
uspto-grants-2007_01
Patent number
US07157585B2

Reaction notes

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