Sodium Hydroxide → HCID 54429514, compound

HRID 850418Notes

Reaction equation

HRID 850418 reaction equation
[CH3:1][C:2]([C:10]1[CH:11]=[C:12]([C:18]2[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:22][C:23]([O:25]C)=[O:24])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+]>CO>[CH3:9][C:2]([C:10]1[CH:11]=[C:12]([C:18]2[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:22][C:23]([OH:25])=[O:24])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53761509HCID 53761509, compound

Product 1

HCID 54429514HCID 54429514, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-[3-(1,1-dimethylheptyl)-4-methoxyphenyl]cinnamate (334.5 mg, 1.05 mmol), methanol (4 ml) and a 1N aqueous sodium hydroxide solution (1.2 ml, 1.2 mmol) were mixed, and this solution was refluxed under heating for 1 hour. Methanol was evaporated under reduced pressure. Conc. hydrochloric acid (0.3 ml) and saturated brine (5 ml) were added, and the aqueous layer was extracted 4 times with ethyl acetate (5 ml). The organic layers were combined, washed twice with saturated brine (5 ml), and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained crystals were washed with hexane to give 3-[3-(1,1-dimethylheptyl)-4-methoxyphenyl]cinnamic acid (0.33 g, quant.) as colorless crystals.

Workup

  1. temperaturethis solution was refluxed
  2. temperatureunder heating for 1 hour
  3. customMethanol was evaporated under reduced pressure
  4. additionConc. hydrochloric acid (0.3 ml) and saturated brine (5 ml) were added
  5. extractionthe aqueous layer was extracted 4 times with ethyl acetate (5 ml)
  6. washwashed twice with saturated brine (5 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. washThe obtained crystals were washed with hexane

Sources & evidence

ORD record
ord-3bd5bfe90b0f4ca7be45c7c236950280
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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