Dimedone → 2-((dimethylamino)methylene)-5,5-dimethylcyclohexane-1,3-dione

HRID 2366488Notes

Reaction equation

HRID 2366488 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[CH2:3]1.CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:13][N:14]([CH:16]=[C:5]1[C:6](=[O:8])[CH2:7][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]1=[O:9])[CH3:15]

Participants

3

Reactant 2

HCID 31358DimedoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 6898502-((dimethylamino)methylene)-5,5-dimethylcyclohexane-1,3-dioneYield 46%

Procedure

According to Scheme 2 Step 1: A solution of 5,5-dimethylcyclohexane-1,3-dione (428 mmol, 60 g) and of 1,1-dimethoxy-N,N-dimethylmethanamine (514 mmol, 68.2 mL) was stirred at room temperature for 1 hour. After evaporation and trituration in cyclohexane, 38.5 g (197 mmol, 46%) of 2-((dimethylamino)methylene)-5,5-dimethylcyclohexane-1,3-dione were obtained as a pale yellow solid.

Workup

  1. customAfter evaporation and trituration in cyclohexane

Sources & evidence

ORD record
ord-ffef04bdbcd24a6ea623bae8ef110598
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

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