Hydrochloric Acid → HCID 54241326, compound

HRID 466328Notes

Reaction equation

HRID 466328 reaction equation
[CH3:1][Si: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.[OH-].[Na+].Cl>O1CCCC1.O>[CH3:13][Si: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 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15294Methyl 4-FormylbenzoateHCID 117454861-(3-(Trimethylsilyl)phenyl)ethanone

Product 1

HCID 54241326HCID 54241326, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 130 mg (0.676 mmol) of 3'-trimethylsilylacetophenone and 127 mg (0.774 mmol) of methyl 4-formylbenzoate in 4.5 ml of tetrahydrofuran (THF) were added 128 mg (3.20 mmol) of NaOH and 3 ml of hot water, and the mixture was stirred at room temperature overnight. The reaction mixture was adjusted with 7 ml of 0.5N-HCl to pH6, and then the aqueous solution was extracted with ethyl acetate. The extract was washed with 0.05N-HCl and H2O, dried and evaporated. The residue was purified by column chromatography affording 133 mg of pale yellow powder (yield 61%), which was recrystallized from a mixture of methylene chloride, methanol and n-hexane to give 98 mg of pale yellow needles, m.p. 179°-180° C. (yield 45%).

Workup

  1. extractionthe aqueous solution was extracted with ethyl acetate
  2. washThe extract was washed with 0.05N-HCl and H2O
  3. customdried
  4. customevaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-09a5202d668149f0976029343e4d3427
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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