Formaldehyde → HCID 57429416, compound
Reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]([CH:10]([CH3:14])[CH2:11][CH:12]=[O:13])[CH2:5]1)([CH3:3])[CH3:2].C=O.[C:17](O)(=O)CC.N1CCCC1>C(O)(C)C.CC(OC)(C)C>[CH:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]([CH:10]([CH3:14])[C:11](=[CH2:17])[CH:12]=[O:13])[CH2:5]1)([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 45 °C
Procedure
A solution of 3-(3-isopropylcyclohexyl)butanal (6 g, 30.5 mmol) in isopropanol (3.5 mL) followed by formaldehyde (37% wt in water, 30.5 mmol, 1 eq) was charged into a 50 mL three-necked round-bottom flask equipped with a reflux condenser and a mechanical stirrer. Propionic acid (228 L, 3.0 mmol, 0.1 eq) and pyrrolidine (255 L, 3.0 mmol, 0.1 eq) were added at ambient temperature. The reaction mixture was then stirred at 45° C. for 3 h. The crude mixture was cooled to ambient temperature dissolved in MTBE (100 mL) and washed with saturated aqueous NaHCO3 (100 mL), brine (100 mL), dried over magnesium sulphate and concentrated. The crude product was chromatographed on a silica gel column with 3% EtOAc in hexane as elution agent giving 3-(3-isopropylcyclohexyl)-2-methylenebutanal (5 g, gc purity>99%; yield 78%).
Workup
- additionwas charged into a 50 mL three-necked round-bottom flask
- customequipped with a reflux condenser and a mechanical stirrer
- washwashed with saturated aqueous NaHCO3 (100 mL), brine (100 mL)
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
- customThe crude product was chromatographed on a silica gel column with 3% EtOAc in hexane as elution agent
Sources & evidence
- ORD record
- ord-cd542ebc7880482095f1debb09c64df4
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08709994B2
Reaction notes
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