Ethanol → 4-Cyanobenzoic acid

HRID 2304103Notes

Reaction equation

HRID 2304103 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][CH:4]=1)#[N:2].C(O)C.C(=O)([O-])O.[Na+]>O>[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 81589Ethyl 4-cyanobenzoateHCID 516892Sodium Bicarbonate

Product 1

HCID 120874-Cyanobenzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
82 °C

Procedure

A mixture containing ethyl p-cyanobenzoate (87.5 g, 0.5 mol), ethanol (192.5 g), and water (449.2 g) was placed in a 1 l-flask. The mixture was heated to 82° C., and sodium hydrogencarbonate was added thereto so as to adjust the pH of the mixture at 9.0-9.3. Seven hours after the reaction started, liquid chromatographic analysis revealed that the reaction mixture contained 67.6 g of p-cyanobenzoic acid (yield 92%).

Workup

  1. customSeven hours

Sources & evidence

ORD record
ord-f826a29cb8ea4281b3188463e42c14f1
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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