Water → HCID 23050447, compound

HRID 1651821Notes

Reaction equation

HRID 1651821 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[C:15]([O:19][CH3:20])[C:16]=1[O:17][CH3:18])[C:6]([C:8]#[C:9][C:10]([O:12]C)=[O:11])=[O:7].[OH-].[K+].O>O1CCCC1>[CH3:20][O:19][C:15]1[CH:14]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:16]=1[O:17][CH3:18])[C:6]([C:8]#[C:9][C:10]([OH:12])=[O:11])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 23050476HCID 23050476, compound

Product 1

HCID 23050447HCID 23050447, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.8 g (10 mmol) of methyl 3-(3,4,5-trimethoxybenzoyl)propiolate in 30 ml of tetrahydrofuran was treated slowly at 0° with 28 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 evaporated. Crystallization of the residue from methylene chloride/ether/hexane yielded 3-(3,4,5-trimethoxybenzoyl)-propiolic acid of melting point 130°-132°.

Workup

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

Sources & evidence

ORD record
ord-3923fb0a3e9e4db2bea997f844ad61a0
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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