Sodium Hydroxide → HCID 54113384, compound

HRID 850430Notes

Reaction equation

HRID 850430 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:5]([C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=2)[CH:12]=[CH:13][C:14]([O:16]C)=[O:15])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[C:4]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:5]([C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=2)[CH:12]=[CH:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53977325HCID 53977325, compound

Product 1

HCID 54113384HCID 54113384, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-(3-methoxy-2-pentyloxyphenyl)cinnamate (1.47 g, 5.28 mmol), ethanol (10 ml) and a 1N aqueous sodium hydroxide solution (10 ml) were mixed, and this solution was refluxed under heating for 0.5 hour. Ethanol was evaporated under reduced pressure, and conc. hydrochloric acid was added to make the mixture acidic (pH=1). The precipitated crystals were extracted 3 times with ethyl acetate (20 ml). The organic layers were combined, washed 3 times with saturated brine (20 ml), and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by recrystallization from ethanol to give 3-(3-methoxy-2-pentyloxyphenyl)cinnamic acid (1.09 g, 78%) as colorless crystals.

Workup

  1. temperaturethis solution was refluxed
  2. temperatureunder heating for 0.5 hour
  3. customEthanol was evaporated under reduced pressure, and conc. hydrochloric acid
  4. additionwas added
  5. extractionThe precipitated crystals were extracted 3 times with ethyl acetate (20 ml)
  6. washwashed 3 times with saturated brine (20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe drying agent was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-1c4d41af43f642b9a430ae370f4d8edf
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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