Acetic Acid → HCID 67164001, compound

HRID 537339Notes

Reaction equation

HRID 537339 reaction equation
[CH3:1][C:2](C)([C:5](=O)[C:6](=O)[C:7]([CH3:11])([CH3:10])[CH2:8][CH3:9])CC.[C:15]([O-])(=O)[CH3:16].[NH4+:19].[C:20](=O)(O)[O-].[Na+].[C:25](O)(=O)[CH3:26]>>[C:7]([C:6]1[NH:19][C:1]([C:25]([CH2:15][CH3:16])([CH3:26])[CH3:20])=[CH:2][CH:5]=1)([CH2:8][CH3:9])([CH3:11])[CH3:10]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 86653609HCID 86653609, compound

Product 1

HCID 67164001HCID 67164001, compound

Procedure

33.6 g (0.146 mol) of 3,3,6,6-tetramethyl-4,5-octanedione, 22.51 g (0.292 moles) of ammonium acetate and 50.1 mL (0.0.876 moles) of acetic acid were refluxed to 140° C. overnight. The resulting product mixture was neutralized with sodium bicarbonate solution, then extracted with hexanes. The aqueous layer was washed 3× with 100 mL of hexanes. The hexane layer was washed 3× with 100 mL of water then stood over 20 g of anhydrous magnesium sulfate for 2 hrs then removed by filtration. Hexanes was then removed by vacuum, yield 27.6 g (92%). Characterized by Mass Spectrometry: Parent ion at 207 m.u

Workup

  1. extractionextracted with hexanes
  2. washThe aqueous layer was washed 3× with 100 mL of hexanes
  3. washThe hexane layer was washed 3× with 100 mL of water
  4. customthen removed by filtration
  5. customHexanes was then removed by vacuum, yield 27.6 g (92%)

Sources & evidence

ORD record
ord-7ae308d7d6844cf88defd6b5bc2cd007
Source dataset
uspto-grants-2014_10
Patent number
US08859785B2

Reaction notes

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