Hydrochloric Acid → 2-Carboxy-7-(2,3-epoxypropoxy)benzofuran

HRID 1906435Notes

Reaction equation

HRID 1906435 reaction equation
[O:1]1[CH2:19][CH:2]1[CH2:3][O:4][C:5]1[C:13]2[O:12][C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[OH-].[K+].Cl>C(O)C>[C:14]([C:11]1[O:12][C:13]2[C:5]([O:4][CH2:3][CH:2]3[O:1][CH2:19]3)=[CH:6][CH:7]=[CH:8][C:9]=2[CH:10]=1)([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 202119967-(2,3-Epoxypropoxy)-2-ethoxycarbonylbenzofuran

Product 1

HCID 137294122-Carboxy-7-(2,3-epoxypropoxy)benzofuran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

There was dissolved 2.6 g (0.01 mole) of 7-(2,3-epoxypropoxy)-2-ethoxycarbonylbenzofuran obtained in Reference Example 9 in 10 ml of ethanol, and thereto 0.9 g (0.012 mole) of potassium hydroxide in 5 ml of ethanol solution was added dropwise with stirred under cooling with ice. After stirring the mixture for 3 hours the reaction was completed to neutralize the reaction mixture by 2N hydrochloric acid. Thereafter, the solvent was distilled away from the reaction mixture under reduced pressure, the resultant residue was extracted from 30 ml of chloroform. After washing the chloroform layer with water the layer was dried with magnesium sulfate, and then chloroform was distilled away under reduced pressure to give the resultant residue.

Workup

  1. temperatureunder cooling with ice
  2. stirringAfter stirring the mixture for 3 hours the reaction
  3. distillationThereafter, the solvent was distilled away from the reaction mixture under reduced pressure
  4. extractionthe resultant residue was extracted from 30 ml of chloroform
  5. washAfter washing the chloroform layer with water the layer
  6. dry with materialwas dried with magnesium sulfate
  7. distillationchloroform was distilled away under reduced pressure

Sources & evidence

ORD record
ord-3bae652913854429b6fd373248e5a650
Source dataset
uspto-grants-1987_03
Patent number
US04652566

Reaction notes

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