Ethyl Acetate → 4-Formyl-2-nitrobenzoic acid

HRID 924991Notes

Reaction equation

HRID 924991 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9]C(C#N)=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1)=[O:2].CC[O:16][C:17]([CH3:19])=[O:18]>S(=O)(=O)(O)O.O>[CH:1]([C:3]1[CH:10]=[CH:9][C:19]([C:17]([OH:16])=[O:18])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1)=[O:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 221178154-Formyl-2-nitrobenzonitrile

Product 1

HCID 203514394-Formyl-2-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-formyl-2-nitrobenzonitrile (150 mg, 0.85 mmol) in conc. sulfuric acid (2 mL) and water (4 mL) was heated at 100° C. for 13 hours. Followed standard aqueous/EtOAc workup to give Intermediate 73.

Sources & evidence

ORD record
ord-4bf4b1b81b4c4c0f8f73d76dd3cf44ac
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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