1-(3,3-Dimethylcyclohexyl)ethanone → HCID 86673209, compound

HRID 1042409Notes

Reaction equation

HRID 1042409 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH2:6][CH2:5][CH:4]([C:8](=O)[CH3:9])[CH2:3]1.[C:12](O)(=O)C.[CH:16]([NH2:18])=[NH:17]>C(O)CCC>[CH3:1][C:2]1([CH3:11])[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:9]=[CH:12][N:18]=[CH:16][N:17]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 913881-(3,3-Dimethylcyclohexyl)ethanoneHCID 160693Formamidine acetate

Product 1

HCID 86673209HCID 86673209, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 1-(3,3-dimethyl-cyclohexyl)-ethanone (Herbac®) (10 g, 0.06 mol, commercially available at IFF), formamidine acetate (31 g, 0.3 mol), and butanol (50 mL). The reaction mixture is heated to 130° C. and stirred for 24 hours. The crude mass is washed once with aqueous sulfuric acid (10%, 100 mL) followed by twice with brine (30 mL). Butanol is recovered by roto-evaporation. The crude product is further purified with liquid chromatography (Biotage® system) and then crystallized. Product 4-(3,3-dimethyl-cyclohexyl)-pyrimidine (˜10 g) is obtained.

Workup

  1. customA 100 mL reaction flask
  2. washThe crude mass is washed once with aqueous sulfuric acid (10%, 100 mL)
  3. customButanol is recovered by roto-evaporation
  4. customThe crude product is further purified with liquid chromatography (Biotage® system)
  5. customcrystallized

Sources & evidence

ORD record
ord-e86fc8fab2814011a00a108416cda8ab
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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