Water → HCID 23050474, compound

HRID 1651822Notes

Reaction equation

HRID 1651822 reaction equation
[CH2:1]1[O:17][C:16]2[CH:15]=[CH:14][C:5]([C:6]([C:8]#[C:9][C:10]([O:12]C)=[O:11])=[O:7])=[CH:4][C:3]=2[O:2]1.[OH-].[K+].O>O1CCCC1>[CH2:1]1[O:17][C:16]2[CH:15]=[CH:14][C:5]([C:6]([C:8]#[C:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 23050509HCID 23050509, compound

Product 1

HCID 23050474HCID 23050474, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.9 g (25.4 mmol) of methyl 3-[3,4-(methylenedioxy)benzoyl]propiolate in 60 ml of tetrahydrofuran was treated slowly at 0° with 71 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 is 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 methylene chloride/ ether/hexane yielded 3-[3,4-(methylenedioxy)-benzoyl]propiolic acid of melting point 122°-124°.

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 methylene chloride/ ether/hexane

Sources & evidence

ORD record
ord-1bdaa9cdd9e24da094892dbda148c4cc
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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