Hydrochloric Acid → 1,3-Benzodioxole, 5-(chloromethyl)-
Reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.C1OC2C=CC=CC=2O1.C=O.[ClH:23]>[Cl-].[Zn+2].[Cl-]>[CH2:7]([Cl:23])[C:6]1[CH:1]=[CH:2][C:3]2[O:11][CH2:10][O:9][C:4]=2[CH:5]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A typical process for preparing piperonal from 1,2-methylenedioxybenzene has been reported by P. P. Shorygin et al. [J. Gen. Chem. (U.S.S.R.), 8,975 (1938)]. This is a two-step process. In the first step, 1,2-methylenedioxybenzene is reacted with formalin in petroleum benzine under the influence of hydrogen chloride gas and zinc chloride to form piperonyl chloride (with a 70-78% yield based on the amount of 1,2-methylenedioxybenzene having reacted). This is followed by the second step in which the piperonyl chloride is reacted with an equimolar amount of hexamine in 60% alcohol to give a 70-80% yield of piperonal. By E. D. Laskina et al. [Chemical Abstracts, 57,9714 (1962)], another process has been described in which 1,2-methelenedioxybenzene is reacted with formalin in the presence of a large excess of the sodium salt of m-nitrobenzenesulfonic acid, hydrogen chloride, and an aluminum catalyst to give a 42.4% yield of piperonal.
Sources & evidence
- ORD record
- ord-cae0cf3dbb994694847a15f0c887352c
- Source dataset
- uspto-grants-1979_06
- Patent number
- US04157333
Reaction notes
Loading…