Potassium Hydroxide → HCID 19373470, compound

HRID 256630Notes

Reaction equation

HRID 256630 reaction equation
[OH-].[K+].[C:3]([C:8]1[CH:26]=[C:25]([C:27]([CH2:30][CH3:31])([CH3:29])[CH3:28])[CH:24]=[CH:23][C:9]=1[O:10][C:11]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:12]=1[C:13]([O:15]C)=[O:14])([CH2:6][CH3:7])([CH3:5])[CH3:4]>C(O)C>[C:3]([C:8]1[CH:26]=[C:25]([C:27]([CH2:30][CH3:31])([CH3:29])[CH3:28])[CH:24]=[CH:23][C:9]=1[O:10][C:11]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:12]=1[C:13]([OH:15])=[O:14])([CH2:6][CH3:7])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19373461HCID 19373461, compound

Product 1

HCID 19373470HCID 19373470, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of potassium hydroxide (5.6 g, 0.1 mol) in ethanol (150 mL) was added methyl 2-(2,4-di-tert-pentylphenoxy)-5-methoxybenzoate (18.0 g, 0.045 mol) and the mixture brought to reflux for 2 hours. TLC indicated the hydrolysis to be complete. The ethanol was removed in vacuo and the residue taken up in water (75 mL) and acidified with 6N HCl. The aqueous mixture was extracted with ethyl acetate (3×100 mL). The organic layers were combined and dried over magnesium sulfate, filtered and the solvent removed in vacuo. Recrystallization from heptane yielded the product as a white solid in 90% yield. NMR and mass spectral analysis were consistent with proposed structure.

Workup

  1. temperatureto reflux for 2 hours
  2. customthe hydrolysis
  3. customThe ethanol was removed in vacuo
  4. extractionThe aqueous mixture was extracted with ethyl acetate (3×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customRecrystallization from heptane

Sources & evidence

ORD record
ord-614b4c5e157d40f3a5b204262a16e53d
Source dataset
uspto-grants-1993_11
Patent number
US05258407

Reaction notes

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