Citronellal → HCID 86673208, compound

HRID 1042402Notes

Reaction equation

HRID 1042402 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH2:3][CH:4]=O.[C:12](O)(=O)C.[CH:16]([NH2:18])=[NH:17]>C(O)CCC>[CH3:1][CH:2]([C:3]1[CH:12]=[N:17][CH:16]=[N:18][CH:4]=1)[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 7794CitronellalHCID 160693Formamidine acetate

Product 1

HCID 86673208HCID 86673208, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 3,7-dimethyl-oct-6-enal (Citronellal®) (Commercially available at IFF) (10 g, 0.06 mol), 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 5-(1,5-dimethyl-hex-4-enyl)-pyrimidine (˜5 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-9cff4216ffa34e2f8b86cb6e79957072
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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