Methanol → 5-Chloro-2-(2-chlorophenyl)-benzoxazole-7-propanoic Acid

HRID 842130Notes

Reaction equation

HRID 842130 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][CH2:20][OH:21])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])=[N:7][C:6]=2[CH:17]=1.C[OH:23].O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][C:20]([OH:23])=[O:21])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])=[N:7][C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 226182825-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-propyl)-benzoxazole

Product 1

HCID 226182975-Chloro-2-(2-chlorophenyl)-benzoxazole-7-propanoic AcidYield 72.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10.3 ml (41 mmol of O) of Kiliani solution was added at −10° to −5° C. within 20 minutes to a solution of 6.44 g (20 mmol) of 5-chloro-2-(2-chlorophenyl)-7-(3-hydroxy-propyl)-benzoxazole in 130 mg of acetone. After 45 minutes, 5 ml of methanol and 130 ml of water were added. The acetone was removed in vacuo, the solid suspended, collected, and washed with 1 N sulfuric acid and water. The residue was taken up in 35 ml of 1 N NaOH and 50 ml of water, and extracted with ether. The water phase was acidified with 5 N HCl to pH 3. Filtration and washing gave the title compound (4.88 g, 72.6%), mp 152-4° C.

Workup

  1. customThe acetone was removed in vacuo
  2. customcollected
  3. washwashed with 1 N sulfuric acid and water
  4. extraction50 ml of water, and extracted with ether
  5. filtrationFiltration
  6. washwashing

Sources & evidence

ORD record
ord-722a2a93f1c5438b9ec997750d15b260
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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