Sodium Hydroxide → HCID 54179635, compound

HRID 1723081Notes

Reaction equation

HRID 1723081 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=[CH:17][C:18]([O:20]COCC)=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][O:11][CH2:12][CH3:13].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=[CH:17][C:18]([OH:20])=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][O:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54185882HCID 54185882, compound

Product 1

HCID 54179635HCID 54179635, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.00 g (17.8 mmol) of the ester was dissolved in 120 ml of methanol. To the resulting solution was added 30 ml of an aqueous solution containing 3.60 g of sodium hydroxide at room temperature. The mixture was left to stand at room temperature overnight. Methanol was distilled off from the reaction mixture under reduced pressure and the residue was made acidic with hydrochloric acid under ice cooling. The mixture was extracted three times with chloroform. The extract organic layer was washed with water and subsequently dried over anhydrous sodium sulfate. The solvent was distilled off from the extract under reduced pressure to afford 4.320 g (15.5 mmol) of 5-(3-methoxy-4-ethoxymethoxyphenyl)-2,4-pentadienoic acid.

Workup

  1. waitThe mixture was left
  2. distillationMethanol was distilled off from the reaction mixture under reduced pressure
  3. extractionThe mixture was extracted three times with chloroform
  4. washThe extract organic layer was washed with water
  5. dry with materialsubsequently dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off from the
  7. extractionextract under reduced pressure

Sources & evidence

ORD record
ord-e6dd4dae67c34f2abb8321d8927ed9f7
Source dataset
uspto-grants-1989_08
Patent number
US04859673

Reaction notes

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