Water → HCID 23050494, compound

HRID 1651824Notes

Reaction equation

HRID 1651824 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:4]=1[C:5]([C:7]#[C:8][C:9]([O:11]C)=[O:10])=[O:6].[OH-].[K+].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:4]=1[C:5]([C:7]#[C:8][C:9]([OH:11])=[O:10])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 23050484HCID 23050484, compound

Product 1

HCID 23050494HCID 23050494, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5 g (20 mmol) of methyl 3-(2,5-dimethoxybenzoyl)propiolate in 50 ml of tetrahydrofuran was treated slowly at 0° with 56 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. Crystallization of the residue from ether/hexane yielded 3-(2,5-dimethoxybenzoyl)propiolic acid of melting point 91°-93°.

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. customCrystallization of the residue from ether/hexane

Sources & evidence

ORD record
ord-caf418966b284cada1a62446de767f45
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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