Hydrochloric Acid → 2-(4-Chlorophenyl)benzoxazole-4-carboxylic acid

HRID 969823Notes

Reaction equation

HRID 969823 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1.C1COCC1.[OH-].[Li+].Cl>C(OCC)(=O)C.O.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68459315Methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate

Product 1

HCID 596258542-(4-Chlorophenyl)benzoxazole-4-carboxylic acidYield 90.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 100 mL round bottom flask equipped with a magnetic stirrer was charged with methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate (0.50 g, 1.74 mmol), THF (10 mL), methanol (10 mL), lithium hydroxide (0.08 g, 3.48 mmol) and water (10 mL). The reaction was stirred at room temperature for 18 hours. After this time, the reaction was diluted with ethyl acetate (50 mL) then acidified to pH 4 with 2 N HCl. The aqueous layer was extracted with ethyl acetate (2×25 mL). The organic layers were then combined and washed with brine (1×25 mL), dried with sodium sulfate, filtered and concentrated to dryness in vacuo to yield 2-(4-chlorophenyl)benzoxazole-4-carboxylic acid (0.43 g, 90% yield) as a white solid: 1H NMR (500 MHz, CDCl3) δ 11.53 (bs, 1H), 8.26 (d, J=8.5 Hz, 2H), 8.18 (d, J=8.0 Hz, 1H), 7.84 (d, J=8.0 Hz, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.55 (t, J=8.0 Hz, 1H); MS (ESI) m/z 274 [M+H]+

Workup

  1. customA 100 mL round bottom flask equipped with a magnetic stirrer
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×25 mL)
  3. washwashed with brine (1×25 mL)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-9e73c2c79d2046bd8283d423ac1e78e8
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

Loading…