Propanal → Propane, 1,1-diethoxy-
Reaction equation
[CH3:1][C:2]1C=NNC=1.C(=O)CC.[CH:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])OCC.[N+]([O-])([O-])=O.[NH4+]>C(O)C>[CH2:19]([O:18][CH:11]([O:15][CH2:16][CH3:17])[CH2:1][CH3:2])[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In the first step of the present synthesis of 4-MP, propionaldehyde is reacted with triethyl orthoformate in the presence of ethanol and ammonium nitrate to produce 1,1-diethoxypropane. In the second step, the 1,1-diethoxypropane produced in the first step is reacted neat (without a solvent) with a catalyst, which comprises an acid and an amine, to produce 1-ethoxy-1-propene (ethyl-1-propenyl ether). In the third step, this material is purified by washing and drying, without distillation. In the fourth step, the 1-ethoxy-1-propene from the third step is reacted with triethyl orthoformate in the presence of boron trifluoride-diethyl etherate to produce 1,1,3,3-tetraethoxy-2-methyl propane (“TEMP”). In the fifth step, the TEMP from the third step is reacted with hydrazine or a hydrazonium salt or hydrazine hydrate at elevated temperatures to produce 4-methylpyrazole.
Sources & evidence
- ORD record
- ord-ae435f0adc504513ad775c0f5fd5fde1
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07553863B2
Reaction notes
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