Water → HCID 23050485, compound

HRID 1651823Notes

Reaction equation

HRID 1651823 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([C:9]#[C:10][C:11]([O:13]C)=[O:12])=[O:8])=[CH:5][CH:4]=1.[OH-].[K+].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]#[C:10][C:11]([OH:13])=[O:12])=[O:8])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 18991480HCID 18991480, compound

Product 1

HCID 23050485HCID 23050485, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.2 g (28 mmol) of methyl 3-(4-methoxybenzoyl)propiolate in 60 ml of tetrahydrofuran was treated slowly at 0° with 80 ml of 3% potassium hydroxide solution and stirred at 0° for a further 1 hour. The reaction mixture was treated with water and extracted once with ether. The ether phase was discarded. The aqueous phase was adjusted to pH 1 with 1N hydrochloric acid and extracted twice with ether. The combined organic phases were dried over sodium sulphate and concentrated. Precipitation of the residue from methylene chloride/ether/hexane yielded 3-(4-methoxybenzoyl)propiolic acid as an amorphous powder.

Workup

  1. extractionextracted once with ether
  2. extractionextracted twice with ether
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated
  5. customPrecipitation of the residue from methylene chloride/ether/hexane

Sources & evidence

ORD record
ord-013cba0c51e5406ca39d98ee1d1736fd
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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