Hydrochloric Acid → Benzoyl chloride

HRID 1968442Notes

Reaction equation

HRID 1968442 reaction equation
[C:1]1([C:7]2[O:8]C3C=C(C(O)=O)C=CC=3N=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2OC3C=C(C(OC)=O)C=CC=3N=2)C=CC=CC=1.[Li+].[OH-].[ClH:40]>C1COCC1.CO.O>[C:7]([Cl:40])(=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10586965Methyl 2-phenyl-benzoxazole-6-carboxylateHCID 109007142-Phenyl-1,3-benzoxazole-6-carboxylic acid

Product 1

HCID 7412Benzoyl chloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Phenyl-benzooxazole-6-carboxylic acid, 1v. 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

  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-2ef193be53934a3fbc01b045f5fe7dee
Source dataset
uspto-grants-2013_04
Patent number
US08426401B2

Reaction notes

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