Potassium Hydroxide → HCID 22237485, compound

HRID 324097Notes

Reaction equation

HRID 324097 reaction equation
C([O:3][C:4](=[O:31])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[CH:12]=2)[C:8]([O:19][CH2:20][O:21][CH3:22])=[C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[O:30])[CH:24]=2)[CH:6]=1)C.[OH-].[K+]>CO.Cl.O>[CH:17]([C:13]1[CH:12]=[C:11]([C:9]2[CH:10]=[C:5]([CH:6]=[C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[O:30])[CH:24]=3)[C:8]=2[O:19][CH2:20][O:21][CH3:22])[C:4]([OH:31])=[O:3])[CH:16]=[CH:15][CH:14]=1)=[O:18]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 54135330HCID 54135330, compound

Product 1

HCID 22237485HCID 22237485, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3,5-bis-(3-formylphenyl)-4-methoxymethoxybenzoic acid ethyl ester (960 mg, 2.12 mmol) in 3 mL MeOH was added 3 mL H2O and solid KOH (179 mg, 3.18 mmol). The reaction was refluxed for 5 to 6 hours then the cooled reaction mixture was diluted with 2N HCl and water. The aqueous solution was extracted with EtOAc (3×) and the combined organic layers were dried over Na2SO4. The solvent was removed in vacuo to give an oil that was flash chromatographed (10% MeOH:90% EtOAc) on silica gel. There yielded 650 mg of the desired acid along with some of the methyl ester of the desired acid. The methyl ester was resubjected to reaction conditions to give more of the desired acid for a total yield of 690 mg, 76.6%. 1H NMR (CDCl3) δ2.63 (s, 3H); 4.19 (s, 2H); 7.65 (t, J=7.36 Hz, 2H); 7.87-7.95 (m, 4H); 8.06-8.26 (m, 4H); 10.10 (s, 2H).

Workup

  1. temperatureThe reaction was refluxed for 5 to 6 hours
  2. customthe cooled reaction mixture
  3. extractionThe aqueous solution was extracted with EtOAc (3×)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customto give an oil that
  7. customchromatographed (10% MeOH:90% EtOAc) on silica gel

Sources & evidence

ORD record
ord-739a3c3cc0734b7ebd518060ede99a2b
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Reaction notes

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