Sodium Hydroxide → HCID 54566711, compound

HRID 850425Notes

Reaction equation

HRID 850425 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=1[C:18]1[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=1)[CH:21]=[CH:22][C:23]([O:25]C)=[O:24].[OH-].[Na+]>C(O)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=1[C:18]1[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=1)[CH:21]=[CH:22][C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54425961HCID 54425961, compound

Product 1

HCID 54566711HCID 54566711, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-(1-bromo-4-pentyloxynaphthalene-2-yl)cinnamate (588 mg, 1.56 mmol), ethanol (4 ml) and a 1N aqueous sodium hydroxide solution (4 ml) were mixed, and this solution was refluxed under heating for 1 hour. Ethanol was evaporated under reduced pressure and conc. hydrochloric acid was added to make the reaction mixture acidic. THF (5 ml) and ethyl acetate (20 ml) were added to dissolve the precipitated crystals. The organic layer was separated and the aqueous layer was extracted twice 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 washing with hexane to give 3-(1-bromo4-pentyloxynaphthalene-2-yl)cinnamic acid (540 mg, 95%) as pale-yellow crystals.

Workup

  1. temperaturethis solution was refluxed
  2. temperatureunder heating for 1 hour
  3. customEthanol was evaporated under reduced pressure and conc. hydrochloric acid
  4. additionwas added
  5. additionTHF (5 ml) and ethyl acetate (20 ml) were added
  6. dissolutionto dissolve the precipitated crystals
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted twice with ethyl acetate (20 ml)
  9. washwashed 3 times with saturated brine (20 ml)
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationThe drying agent was filtered off
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customThe obtained residue was purified
  14. washby washing with hexane

Sources & evidence

ORD record
ord-a03b59a4ad634a24829f5d8417168779
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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