Sodium Hydroxide → HCID 54527591, compound

HRID 850442Notes

Reaction equation

HRID 850442 reaction equation
[CH2:1]([C:7]1[CH:8]=[C:9]([C:15]2[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=2)[CH:18]=[CH:19][C:20]([O:22]C)=[O:21])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[Na+]>C(O)C>[CH2:1]([C:7]1[CH:8]=[C:9]([C:15]2[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=2)[CH:18]=[CH:19][C:20]([OH:22])=[O:21])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53798189HCID 53798189, compound

Product 1

HCID 54527591HCID 54527591, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-(3-hexyl-4-methoxyphenyl)cinnamate (80 mg, 0.29 mmol), ethanol (1 ml) and a 1N aqueous sodium hydroxide solution (1 ml) were mixed, and this solution was refluxed under heating for 1.5 hours. Ethanol was evaporated under reduced pressure, and conc. hydrochloric acid was added to make the solution acidic. Ethyl acetate (5 ml) was added to dissolve the precipitated crystals. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate (5 ml). The organic layers were combined, washed 3 times with saturated brine (8 ml), and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate to give 3-(3-hexyl-4-methoxyphenyl)cinnamic acid (58 mg, 76%) as colorless crystals.

Workup

  1. temperaturethis solution was refluxed
  2. temperatureunder heating for 1.5 hours
  3. customEthanol was evaporated under reduced pressure, and conc. hydrochloric acid
  4. additionwas added
  5. additionEthyl acetate (5 ml) was added
  6. dissolutionto dissolve the precipitated crystals
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted twice with ethyl acetate (5 ml)
  9. washwashed 3 times with saturated brine (8 ml)
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationThe drying agent was filtered off
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1b8047cdd0904cf6be8a23bed6c39d7b
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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