Hydrochloric Acid → Benzoyl chloride
Reaction equation
[C:1]1([C:7]2[O:8]C3C=C(C(OC)=O)C=CC=3N=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].O.[ClH:23]>C1COCC1.CO>[C:7]([Cl:23])(=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of methyl 2-phenyl-benzooxazole-6-carboxylate 1u (0.37 g, 1.46 mmol) and LiOH (0.10 g, 4.2 mmol) in THF (4 mL), MeOH (4 mL), and H2O (4 mL) was stirred at room temperature for 6 h. Aqueous 1N HCl solution was added to the mixture to adjust pH to 3-4. The resulting mixture was extracted with EtOAc (2×). The organic solution was washed with aq. NaCl, dried over Na2SO4 and concentrated to give 1t (0.34 g).
Workup
- extractionThe resulting mixture was extracted with EtOAc (2×)
- washThe organic solution was washed with aq. NaCl
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-25222ae32845496db24ffcbb025de782
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623858B2
Reaction notes
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