Hydrochloric Acid → 3-(4-Cyanophenyl)-propionic acid

HRID 1978399Notes

Reaction equation

HRID 1978399 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13]CC)=[O:12])=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].Cl>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11435631Ethyl 3-(4-cyanophenyl)propanoate

Product 1

HCID 93617423-(4-Cyanophenyl)-propionic acidYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-(4-cyanophenyl)propionate (6.00 g, 29.5 mmol), 2N-sodium hydroxide (30 ml, 60.0 mmol) and ethanol (60 ml) was stirred at room temperature for 1 hour. The reaction mixture was acidified with 1N-hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over MgSO4 and concentrated in vacuo to give 3-(4-cyanophenyl)propionic acid as colorless crystals (4.40 g, 85%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-987d372335c54bf89eeab534ed1de684
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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