Nitrogen → Heptanoic acid, 6-oxo-, methyl ester

HRID 1189355Notes

Reaction equation

HRID 1189355 reaction equation
N#N.[C:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])(=[O:5])[CH3:4].OS(O)(=O)=O.[C:18]([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CO>[CH3:18][O:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][C:3](=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 947NitrogenHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 988106-Oxoheptanoic acid

Product 1

HCID 288022Heptanoic acid, 6-oxo-, methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask under inert atmosphere (N2), a solution of 5-acetylvaleric acid (7.54 g, 50.21 mmol) in a mixture of CH2Cl2 (35 mL) and MeOH (14 mL) was treated with conc. H2SO4 (0.14 mL, 2.51 mmol) and the reaction mixture was stirred at reflux for 24 h. The mixture was cooled to rt and sat. aq. Na2CO3 was added. The aq. layer was extracted with CH2Cl2 and the combined organic layers were washed with water, dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:1→1:2 hept-EA) gave the title compound as an orange oil.

Workup

  1. temperatureat reflux for 24 h
  2. extractionThe aq. layer was extracted with CH2Cl2
  3. washthe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (50:1→1:2 hept-EA)

Sources & evidence

ORD record
ord-9c129146c08a4e97816b795c453dac9b
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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