Hydrochloric Acid → 3-(1,3-oxazol-5-yl)benzoic Acid
Reaction equation
[C:1]([O-:4])([O-])=[O:2].[K+].[K+].[N+:7](CS(C1C=CC(C)=CC=1)(=O)=O)#[C-:8].C([C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[C:25]([O:27][CH3:28])=O)=O.Cl>CO>[O:27]1[C:25]([C:24]2[CH:29]=[C:30]([CH:31]=[CH:22][CH:23]=2)[C:1]([OH:4])=[O:2])=[CH:8][N:7]=[CH:28]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
MeOH (54 mL) was added to a round bottom flask containing K2CO3 (6.74 gm, 48.70 mmol), 1-(isocyanomethylsulfonyl)-4-methylbenzene (5.00 gm, 25.60 mmol), and methyl 3-formylbenzoate (4.00 gm, 24.37 mmol). The reaction mixture was heated at 80° C. for 3 h and then stirred at rt overnight. The mixture was concentrated under reduced pressure. The remaining residue was partitioned between EtOAc and water. The aqueous solution was isolated and acidified using 1N HCl. The acidified aqueous phase was extracted with EtOAc (2×). The organic extracts were combined, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give the product, 3-(oxazol-5-yl)benzoic acid, (4.00 gm, 21.15 mmol, 86% yield) as a white solid. Anal. Calcd. for C10H7NO3 m/z 189.0, found: 190.1 (M+H)+. Crude product was used without purification.
Workup
- concentrationThe mixture was concentrated under reduced pressure
- customThe remaining residue was partitioned between EtOAc and water
- customThe aqueous solution was isolated
- extractionThe acidified aqueous phase was extracted with EtOAc (2×)
- washwashed with saturated aqueous NaCl
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5554dc387d534ff7bd6f151ecc54dd1b
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815909B2
Reaction notes
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