Hydrochloric Acid → HCID 11356889, compound

HRID 2364911Notes

Reaction equation

HRID 2364911 reaction equation
[NH2-].[Li+].[CH3:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:12]([O:18]CC)(=O)[CH2:13][CH2:14][CH2:15][CH3:16].Cl.[C:22](OC)(C)(C)[CH3:23]>>[CH3:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4](=[O:11])[CH2:3][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:22][CH3:23]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 80932-OctanoneHCID 10882Ethyl valerateHCID 15413tert-Butyl methyl ether3×HCID 24532Lithium amide

Product 1

HCID 11356889HCID 11356889, compound

Procedure

Lithium amide (12.4 g, 498 mmol) was dissolved in 130 mL of methyl t-butyl ether (MTBE), and a solution of 32.4 g (253 mmol) of octan-2-one in MTBE (67 mL) was dropped under a nitrogen atmosphere at 35° C. and the mixture was stirred for 1 hour. Then, into this was dropped a solution of 80.0 g (506 mmol) of ethyl pentanoate in MTBE (67 mL), and the mixture was stirred at 35° C. for 4.5 hours. After cooling, the resultant mixed liquid was added into concentrated hydrochloric acid containing ice added, and the oil phase was extracted and died over sodium sulfate, then, concentrated. For purification of the resultant concentrate, a copper acetate aqueous solution was added to cause crystallization of a copper complex of the concentrate, which was dissolved in MTBE and mixed with a sulfuric acid aqueous solution and the mixture was returned to the concentrate, and the oil phase was extracted and dried over sodium sulfate and concentrated, to obtain 36.3 g (151 mmol) of pentadecane-7,9-dione.

Workup

  1. stirringthe mixture was stirred at 35° C. for 4.5 hours
  2. temperatureAfter cooling
  3. additionthe resultant mixed liquid
  4. additioncontaining ice
  5. additionadded
  6. extractionthe oil phase was extracted
  7. concentrationconcentrated
  8. customFor purification of the resultant
  9. concentrationconcentrate
  10. additiona copper acetate aqueous solution was added
  11. customcrystallization of a copper complex of the concentrate, which
  12. dissolutionwas dissolved in MTBE
  13. additionmixed with a sulfuric acid aqueous solution
  14. extractionthe oil phase was extracted
  15. dry with materialdried over sodium sulfate
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-ddf513cf3c494c6881c2ae61c4f9db30
Source dataset
uspto-grants-2014_04
Patent number
US08697256B2

Reaction notes

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