Sulfuric Acid → HCID 53841322, compound

HRID 1491665Notes

Reaction equation

HRID 1491665 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[O:11][CH:12]=2)=[CH:4][CH:3]=1.[CH:18](O)([CH3:20])[CH3:19].S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[O:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 18953969HCID 18953969, compound

Product 1

HCID 53841322HCID 53841322, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-(4-chlorophenyl)-2-oxazolepropionic acid (0.5 g) and isopropanol (30 ml) was added conc. sulfuric acid (0.3 ml), and the resultant was refluxed for 5 hours. The reaction mixture was poured into water and extracted with ether. The ether layer was washed succesively with a saturated sodium hydrogen carbonate aqueous solution and water, and dried over MgSO4. The ether was distilled off to give crystals of isopropyl 4-(4-chlorophenyl)-2-oxazolepropionate (530 mg, 91%). Recrystallization from hexane gave colorless prism crystals of mp 30°-31° C.

Workup

  1. temperaturethe resultant was refluxed for 5 hours
  2. extractionextracted with ether
  3. washThe ether layer was washed succesively with a saturated sodium hydrogen carbonate aqueous solution and water
  4. dry with materialdried over MgSO4
  5. distillationThe ether was distilled off

Sources & evidence

ORD record
ord-72bce16bf963414b8a36bb215b5c7d21
Source dataset
uspto-grants-1994_12
Patent number
US05371098

Reaction notes

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