Water → HCID 19074098, compound

HRID 964910Notes

Reaction equation

HRID 964910 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:8])[CH2:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6416PinacoloneHCID 14307Methyl 4-chlorobenzoateHCID 24758Sodium hydride

Product 1

HCID 19074098HCID 19074098, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

30 g of methyl 4-chlorobenzoate was dissolved in anhydrous THF, and 16.9 g of 60% sodium hydride was added under cooling with ice. 21.1 g of pinacolone was added dropwise, and the mixture was stirred under heating at 50° C. for 6 hours. Then, 100 ml of water was added dropwise under cooling with ice, and the solvent was distilled off under reduced pressure. 200 ml of water and 100 ml of 6N hydrochloric acid were added thereto, and then extraction with ethyl acetate was carried out. The extract layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: chloroform/hexane=2/8) to obtain 43 g of the desired product as a viscous liquid. nD20.0 1.5012

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. distillationthe solvent was distilled off under reduced pressure
  4. addition200 ml of water and 100 ml of 6N hydrochloric acid were added
  5. extractionextraction with ethyl acetate
  6. dry with materialThe extract layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (developing solvent: chloroform/hexane=2/8)

Sources & evidence

ORD record
ord-cbe34f3cae244cebb2b8a1a8294f21b0
Source dataset
uspto-grants-1998_06
Patent number
US05773388

Reaction notes

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