Hydrochloric Acid → 2-Phenyl-1,3-benzoxazole-6-carboxylic acid

HRID 409925Notes

Reaction equation

HRID 409925 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[C:14]([C:16]([O:18]C)=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].O.Cl>C1COCC1.CO>[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 10586965Methyl 2-phenyl-benzoxazole-6-carboxylate

Product 1

HCID 109007142-Phenyl-1,3-benzoxazole-6-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-phenyl-benzoxazole-6-carboxylate 25c (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 25d (0.34 g).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×)
  2. washThe organic solution was washed with aq. NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9cd99bf9a4c34d62a9a30d766d195903
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

Loading…