Acetic Acid → HCID 10610637, compound

HRID 1420875Notes

Reaction equation

HRID 1420875 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=O)[CH2:3]1.[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:11])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[C:14]([C:12]#[N:13])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 843993,3,5,5-TetramethylcyclohexanoneHCID 517165Ammonium Acetate

Product 1

HCID 10610637HCID 10610637, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The mixture of 3,3,5,5-tetramethylcyclohexanone (2-13) (2.64g, 17 mmol), ethyl cyanoacetate (1.93, 17 mmol), acetic acid (0.2 ml) and ammonium acetate (0.2 g) in benzene (6.4 ml) was refluxed with a Dean-Stark aparatus for 10 h. To this benzene (30 ml) and saline (30 ml) was added, organic layer separated, dried over Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography, eluting with hexane to give 2.0 g (50%) of (16) as an oil.

Workup

  1. temperaturewas refluxed with a Dean-Stark aparatus for 10 h
  2. customorganic layer separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography
  7. washeluting with hexane

Sources & evidence

ORD record
ord-d627afa9cbdb4892b84da36aa77547b0
Source dataset
uspto-grants-2000_06
Patent number
US06071966

Reaction notes

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