Methanol → 3-Cyano-5-iodobenzoic acid
Reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[C:6]([C:11]#[N:12])[CH:5]=1.[Li+].[OH-].CO>O1CCCC1>[C:11]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([I:10])[CH:7]=1)[C:3]([OH:13])=[O:2])#[N:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of methyl-3-cyano-5-iodobenzoate (640 mg, 2.3 mmol) in tetrahydrofuran (8 mL) was treated with 0.5M LiOH (5.5 mL, 2.75 mmol) and methanol. The reaction mixture was heated at reflux for 1 hour. The solvent was concentrated in vacuo and the mixture treated with 1N HCl. The resulting white precipitate was filtered and the filtrate was extracted with dichloromethane. The residue and the extracted filtrate were combined and concentrated in vacuo to afford 590 mg (94%) of 3-cyano-5-iodobenzoic acid, as a white solid.
Workup
- temperatureThe reaction mixture was heated
- temperatureat reflux for 1 hour
- concentrationThe solvent was concentrated in vacuo
- additionthe mixture treated with 1N HCl
- filtrationThe resulting white precipitate was filtered
- extractionthe filtrate was extracted with dichloromethane
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-43e72154a7d94096ab505a130f11a08d
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06660753B2
Reaction notes
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