Water → HCID 81793397, compound

HRID 736847Notes

Reaction equation

HRID 736847 reaction equation
[NH2-].[Na+].[CH3:3][C:4]([CH3:9])([CH3:8])[C:5](=[O:7])[CH3:6].[CH3:10][O:11][CH2:12][C:13](OC)=[O:14].O>C(O)(=O)C>[CH3:10][O:11][CH2:12][C:13](=[O:14])[CH2:6][C:5](=[O:7])[C:4]([CH3:9])([CH3:8])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6416PinacoloneHCID 24533Sodium amideHCID 80507Methyl methoxyacetate

Product 1

HCID 81793397HCID 81793397, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 200 mL-volume flask equipped with a stirrer, a thermometer and a dropping funnel was placed 9.74 g (250 mmol) of sodium amide, and the flask was purged with argon. Then, 80 mL of toluene was placed in the flask. Subsequently, 25.0 g (249.6 mmol) of 3,3-dimethyl-2-butanone was slowly dropped into the flask, and the resulting mixture was stirred for 15 minutes. Into the flask was further dropped 10.4 g (99.9 mmol) of methyl methoxyacetate, and the mixture was stirred for 30 minutes for carrying out a reaction. After the reaction was complete, 50 mL of water was placed in the flask under cooling with ice. The aqueous portion was taken out, neutralized with acetic acid, and subjected to extraction with ether. The ether extract was washed with water, dried over hydrous sodium sulfate, and filtered. The filtrate was concentrated and distilled under reduced pressure (65° C., 426 Pa) to give 5.90 g (yield: 34%) of 1-methoxy-5,5-dimethyl-2,4-hexanedione as colorless liquid.

Workup

  1. customIn a 200 mL-volume flask equipped with a stirrer
  2. customthe flask was purged with argon
  3. stirringthe mixture was stirred for 30 minutes
  4. customa reaction
  5. temperatureunder cooling with ice
  6. extractionsubjected to extraction with ether
  7. extractionThe ether extract
  8. washwas washed with water
  9. dry with materialdried over hydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated
  12. distillationdistilled under reduced pressure (65° C., 426 Pa)

Sources & evidence

ORD record
ord-ae1fa5436d834282bda1581f5c218e8e
Source dataset
uspto-grants-2009_09
Patent number
US07595414B2

Reaction notes

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