Potassium Hydroxide → HCID 23051850, compound

HRID 1651367Notes

Reaction equation

HRID 1651367 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:18])[C:12]#[C:13][C:14]([O:16]C)=[O:15])=[CH:5][CH:4]=1.[OH-].[K+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[C:11](=[O:18])[C:12]#[C:13][C:14]([OH:16])=[O:15])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86743959HCID 86743959, compound

Product 1

HCID 23051850HCID 23051850, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.3 g (21.7 mmol) of methyl (E)-6-(4-methoxyphenyl)-4-oxo-5-hexen-2-ynoate in 70 ml of tetrahydrofuran was treated at 0° within 15 minutes with 48.6 ml (26 mmol) of a 3% aqueous potassium hydroxide solution. The reaction mixture was stirred at 0° for 10 minutes, then diluted with 100 ml of water and extracted once with 100 ml of ether. The organic phase was discarded. The aqueous phase was adjusted to pH 1 by the careful addition of 1N hydrochloric acid and extracted twice with ether. The combined organic phases were washed with water, dried over sodium sulphate and concentrated. Crystallization of the residue from ether/hexane yielded (E)-6-(4-methoxy-phenyl)-4-oxo-5-hexen-2-ynoic acid of melting point 98°-100°.

Workup

  1. extractionextracted once with 100 ml of ether
  2. additionThe aqueous phase was adjusted to pH 1 by the careful addition of 1N hydrochloric acid
  3. extractionextracted twice with ether
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customCrystallization of the residue from ether/hexane

Sources & evidence

ORD record
ord-a09f664667d94236aeba1deecc824798
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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