Water → 3-(2,3,4-Trimethoxybenzoyl)-propiolic acid

HRID 1651820Notes

Reaction equation

HRID 1651820 reaction equation
[CH3:1][O:2][C:3]1[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[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[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[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 23050480Methyl 3-(2,3,4-trimethoxybenzoyl)propiolate

Product 1

HCID 230504433-(2,3,4-Trimethoxybenzoyl)-propiolic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.7 g (9.7 mmol) of methyl 3-(2,3,4-trimethoxybenzoyl)propiolate in 30 ml of tetrahydrofuran was treated slowly at 0° with 27 ml of 3% potassium hydroxide solution and subsequently stirred at 0° for a further 1.5 hours. 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 ethyl acetate/hexane yielded 3-(2,3,4-trimethoxybenzoyl)-propiolic acid of melting point 119°-121°.

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 ethyl acetate/hexane

Sources & evidence

ORD record
ord-7f4cf5b2e2154f579c7206a96cf95bea
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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