Water → 2-Methoxy-6,6-dimethyl-3,5-heptanedione

HRID 736846

Reaction equation

HRID 736846 reaction equation
[NH2-].[Na+].[CH3:3][C:4]([CH3:9])([CH3:8])[C:5](=[O:7])[CH3:6].[CH3:10][O:11][CH:12]([CH3:17])[C:13](OC)=[O:14].O>C(O)(=O)C>[CH3:10][O:11][CH:12]([C:13](=[O:14])[CH2:6][C:5](=[O:7])[C:4]([CH3:9])([CH3:8])[CH3:3])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6416PinacoloneHCID 24533Sodium amideHCID 86599Propanoic acid, 2-methoxy-, methyl ester

Product 1

HCID 249871272-Methoxy-6,6-dimethyl-3,5-heptanedioneYield 52%

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 8.20 g (210 mmol) of sodium amide, and the flask was purged with argon. Then, 80 mL of toluene was placed in the flask. Subsequently, 15.1 g (150.8 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 5.50 g (46.6 mmol) of methyl 2-methoxypropionate (prepared by the method of Reference Example 1), 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 anhydrous sodium sulfate, and filtered. The filtrate was concentrated and distilled under reduced pressure (59° C., 492 Pa) to give 4.50 g (yield: 52%) of 2-methoxy-6,6-dimethyl-3,5-heptanedione as colorless liquid.

Workup

  1. customIn a 200 mL-volume flask equipped with a stirrer
  2. customthe flask was purged with argon
  3. customprepared by the method of Reference Example 1), and the mixture
  4. stirringwas stirred for 30 minutes
  5. customa reaction
  6. temperatureunder cooling with ice
  7. extractionsubjected to extraction with ether
  8. extractionThe ether extract
  9. washwas washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated
  13. distillationdistilled under reduced pressure (59° C., 492 Pa)

Sources & evidence

ORD record
ord-28b2f7864fd24bfebc3c0dba4e1b25e9
Source dataset
uspto-grants-2009_09
Patent number
US07595414B2

Linked notes

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