1,3-Cyclohexanedione → 2-[(Dimethylamino)methylidene]cyclohexane-1,3-dione

HRID 2366484Notes

Reaction equation

HRID 2366484 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>>[CH3:11][N:12]([CH:14]=[C:2]1[C:3](=[O:7])[CH2:4][CH2:5][CH2:6][C:1]1=[O:8])[CH3:13]

Participants

3

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 3593532-[(Dimethylamino)methylidene]cyclohexane-1,3-dioneYield 99.4%

Procedure

According to Scheme 1 Step 1: A solution of cyclohexane-1,3-dione (89 mmol, 10 g) and of 1,1-dimethoxy-N,N-dimethylmethanamine (263 mmol, 35.0 mL) was stirred under reflux for 2 hours. After evaporation, 14.8 g (88.5 mmol, 99%) of 2-((dimethylamino)methylene)cyclohexane-1,3-dione were obtained as a yellow solid.

Workup

  1. temperatureunder reflux for 2 hours
  2. customAfter evaporation

Sources & evidence

ORD record
ord-1ad49646db7f4072af732cca96fae312
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

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