1-Propanol → n-Propyl-5-hydroxybenzoxazole-2-carboxylate

HRID 2248882Notes

Reaction equation

HRID 2248882 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:7]=2[N:8]=1)([OH:3])=[O:2].[CH2:14](O)[CH2:15][CH3:16]>S(=O)(=O)(O)O>[CH2:14]([O:2][C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:7]=2[N:8]=1)=[O:3])[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 10311-PropanolHCID 199946752-Carboxy-5-hydroxybenzoxazole

Product 1

HCID 86745010n-Propyl-5-hydroxybenzoxazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

12.72 g (49.2 mmoles) of 2-carboxy-5-hydroxybenzoxazole is dissolved in 200 ml of n-propanol and 1 drop of concentrated sulfuric acid is added. The mixture is refluxed for 30 hours, concentrated. The resulting solid is suspended in water, neutralized with sodium bicarbonate and filtered, washing the solid with water, then drying. This gives n-propyl-5-hydroxybenzoxazole-2carboxylate which is purified by recrystallization from n-propanol/acetone or by HPLC.

Workup

  1. temperatureThe mixture is refluxed for 30 hours
  2. concentrationconcentrated
  3. filtrationfiltered
  4. washwashing the solid with water
  5. customdrying
  6. customThis gives n-propyl-5-hydroxybenzoxazole-2carboxylate which is purified by recrystallization from n-propanol/acetone or by HPLC

Sources & evidence

ORD record
ord-d0d085ee63aa4284af57944cf079e191
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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