Hydrochloric Acid → 4-[3-(3,5-Bistrimethylgermylphenyl)-3-oxo-1-propenyl]benzoic Acid

HRID 466335Notes

Reaction equation

HRID 466335 reaction equation
[CH3:1][Ge:2]([CH3:17])([CH3:16])[C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([Ge:9]([CH3:12])([CH3:11])[CH3:10])[CH:8]=1.[CH:18]([C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=1)=O.[OH-].[K+].Cl>C(O)(C)C.O1CCCC1>[CH3:11][Ge:9]([CH3:10])([CH3:12])[C:7]1[CH:6]=[C:5]([C:13](=[O:15])[CH:14]=[CH:18][C:20]2[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)[CH:4]=[C:3]([Ge:2]([CH3:16])([CH3:1])[CH3:17])[CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15294Methyl 4-FormylbenzoateHCID 12884911HCID 12884911, compound

Product 1

HCID 1308244-[3-(3,5-Bistrimethylgermylphenyl)-3-oxo-1-propenyl]benzoic AcidYield 53.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3',5'-Bis(trimethylgermyl)acetophenone 163 mg (0.46 mmol) and 96 mg (0.58 mmol) of methyl 4-formylbenzoate was dissolved in 4 ml of a mixture of isopropanol and tetrahydrofuran (1:1). To the mixture was added 2.5 ml of 0.75N aqueous potassium hydroxide solution with stirring and the mixture was stirred at room temperature overnight. The reaction mixture was adjusted to pH3.8 with 0.2N hydrochloric acid and extracted with AcOEt. The extract was evaporated. The residue was purified by column chromatography on silicagel [eluent: methylene chloride-MeOH (10:1)] and recrystallized from a mixture of methylene chloride, MeOH and n-hexane to give 120 mg of yellow prisms, m.p. 194°-195.5° C. (dec.).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionextracted with AcOEt
  3. customThe extract was evaporated
  4. customThe residue was purified by column chromatography on silicagel [eluent: methylene chloride-MeOH (10:1)]
  5. customrecrystallized from a mixture of methylene chloride, MeOH and n-hexane

Sources & evidence

ORD record
ord-0edb72ccc5d94468b76c7c5db85723e6
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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