Hydrochloric Acid → 4-[3-(3-Trimethylgermylphenyl)-3-oxo-1-propenyl]benzoic Acid

HRID 466332Notes

Reaction equation

HRID 466332 reaction equation
[CH3:1][Ge:2]([CH3:13])([CH3:12])[C:3]1[CH:4]=[C:5]([C:9](=[O:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1.[CH:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)=O.Cl>C(O)(C)C.O1CCCC1.[OH-].[K+]>[CH3:13][Ge:2]([CH3:12])([CH3:1])[C:3]1[CH:4]=[C:5]([C:9](=[O:11])[CH:10]=[CH:14][C:16]2[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 15294Methyl 4-FormylbenzoateHCID 146056553'-Trimethylgermylacetophenone

Product 1

HCID 727333434-[3-(3-Trimethylgermylphenyl)-3-oxo-1-propenyl]benzoic AcidYield 23%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

Procedure

3'-Trimethylgermylacetophenone (49 mg, 0.2 mmol) and methyl 4-formylbenzoate (37 mg, 0.23 mmol) was dissolved in 5 ml of a mixture of 50% isopropanol and tetrahydrofuran, 1 ml of 1N aqueous potassium hydroxide solution was added, and the mixture was stirred overnight. The reaction mixture was adjusted to pH1 with 2N hydrochloric acid and extracted with AcOEt. The extract was evaporated and the residue was purified by column chromatography on silica gel (eluent: MeOH-methylene chloride) and recrystallized from a mixture of AcOEt and n-hexane to give 17 mg of pale yellow prisms, m.p. 186°-188° C. (yield 22%).

Workup

  1. additionwas added
  2. extractionextracted with AcOEt
  3. customThe extract was evaporated
  4. customthe residue was purified by column chromatography on silica gel (eluent: MeOH-methylene chloride)
  5. customrecrystallized from a mixture of AcOEt and n-hexane

Sources & evidence

ORD record
ord-03cad5fe91794a56973fe2eef781d402
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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