Hydrochloric Acid → HCID 10845069, compound

HRID 1378972Notes

Reaction equation

HRID 1378972 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6](/[CH:9]=[CH:10]/[C:11]([O:13]C)=[O:12])=[CH:7][CH:8]=1.[OH-].[K+].Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:7][CH:8]=1

Participants

5

Procedure

To 429 mg (2.22 mmol) of methyl (E)-3-(3-methoxy-6-pyridyl)acrylate were added 12 ml of methanol and 1.11 ml of a 4N potassium hydroxide aqueous solution, and the mixture was stirred at room temperature for 20 hours. To the reaction mixture was added 1N hydrochloric acid, and the solution was extracted with ethyl acetate and with chloroform. The ethyl acetate layer and the chloroform layer were separately washed with a saturated aqueous solution of sodium chloride. The combined organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 277 mg (1.55 mmol) of (E)-3-(3-methoxy-6-pyridyl)acrylic acid (yield: 70%).

Workup

  1. extractionthe solution was extracted with ethyl acetate and with chloroform
  2. washThe ethyl acetate layer and the chloroform layer were separately washed with a saturated aqueous solution of sodium chloride
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4596f5db841946af887b32988ea20367
Source dataset
uspto-grants-1997_09
Patent number
US05670492

Reaction notes

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