Benzaldehyde → 2-Methylcinnamic aldehyde
Reaction equation
[CH:1](=[O:4])[CH2:2][CH3:3].[CH:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+]>CO.C(O)(=O)C.O>[CH3:3][C:2](=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:1]=[O:4]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
Propionaldehyde (87 gms 15 moles) was added at 50° C. over a period of 5 hours to a stirred mixture of benzaldehyde (318 gms, 3 moles), methanol (500 mls), water (500 mls) and sodium hydroxide (25 gms). After a further 1 hour stirring at 50° C., the reaction mixture was brought to neutrality with acetic acid and the methanol fractionated out of the reaction. The organic layer was then separated from the aqueous layer and fractionated to recover the excess of benzaldehyde (109 gms, b.pt. 36°-40° C./2 mm Hg) and obtain the -methylcinnamaldehyde (167 gms, b.pt. 100°-102° C./2 mm).
Workup
- customThe organic layer was then separated from the aqueous layer
- customfractionated to recover the excess of benzaldehyde (109 gms, b.pt. 36°-40° C./2 mm Hg)
Sources & evidence
- ORD record
- ord-f75f835ba2bb44e7b4ccddff118281b7
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04486607
Reaction notes
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