Water → 2-Methoxy-3,5-heptanedione

HRID 736850

Reaction equation

HRID 736850 reaction equation
[CH3:1]C(C)([O-])C.[K+].C[O:8][CH:9]([CH3:14])[C:10]([O:12][CH3:13])=O.C[C:16](=[O:19])[CH2:17][CH3:18].O>C(O)(=O)C>[CH3:13][O:12][CH:10]([C:9](=[O:8])[CH2:14][C:16](=[O:19])[CH2:17][CH3:18])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6569Methyl Ethyl KetoneHCID 86599Propanoic acid, 2-methoxy-, methyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 249871312-Methoxy-3,5-heptanedioneYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

In a 200 mL-volume flask equipped with a stirrer, a thermometer and a dropping funnel was placed 25.0 g (223 mmol) of potassium t-butoxide, and the flask was purged with argon. Then, 100 mL of methylcyclohexanone was placed in the flask. Subsequently, 12.5 g (106 mmol) of methyl 2-methoxypropionate (prepared by the method of Reference Example 1) was dropped under cooling with ice, and further 7.70 g (107 mmol) of 2-butanone was slowly dropped. The mixture was cooled to 10° C. and stirred for 30 minutes for carrying out a reaction. After the reaction was complete, 70 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 methylcyclohexane. The methylcyclohexane extract was washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and distilled under reduced pressure (77° C., 1.26 kPa) to give 10.4 g (yield: 62%) of 2-methoxy-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. additionwas dropped
  4. additionwas slowly dropped
  5. customa reaction
  6. temperatureunder cooling with ice
  7. extractionsubjected to extraction with methylcyclohexane
  8. extractionThe methylcyclohexane 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 (77° C., 1.26 kPa)

Sources & evidence

ORD record
ord-1dc7f19806e74dc8875e4596a52c86c4
Source dataset
uspto-grants-2009_09
Patent number
US07595414B2

Linked notes

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