Sodium Hydroxide → HCID 446093, compound

HRID 1756810Notes

Reaction equation

HRID 1756810 reaction equation
[C:1]1([C:7]([O:9]C)=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12616847Methyl cyclohexa-1,3-diene-1-carboxylate

Product 1

HCID 446093HCID 446093, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1,3-cyclohexadiene-1-carboxylate (914 mg, 6.62 mmol) was dissolved in methanol (10 ml) and a 2N aqueous sodium hydroxide solution (4 ml) was added thereto and the solution was stirred at room temperature for 1 hour. The reaction mixture was concentrated, made acidic with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1,3-cyclohexadiene-1-carboxylic acid (761 mg, 92.7%) as white solid. This compound has the following NMR spectrum.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2aef6630bce044c7b16759e894024703
Source dataset
uspto-grants-1995_08
Patent number
US05442062

Reaction notes

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