Piperonyl alcohol → 1,3-Benzodioxole, 5-(chloromethyl)-

Reaction equation

S(Cl)([Cl:3])=O.[CH2:5]1[O:15][C:14]2[CH:13]=[CH:12][C:9]([CH2:10]O)=[CH:8][C:7]=2[O:6]1>>[CH2:5]1[O:15][C:14]2[CH:13]=[CH:12][C:9]([CH2:10][Cl:3])=[CH:8][C:7]=2[O:6]1

Participants

Reactant 2

HCID 10322Piperonyl alcohol

HCID 24386Thionyl Chloride

Product 1

HCID 887131,3-Benzodioxole, 5-(chloromethyl)-

Procedure

153.9 g (1.29 mols) of thionyl chloride are poured onto 65.6 g (0.431 mol) of 3,4-methylenedioxybenzyl alcohol. The mixture is stirred for 90 minutes at ambient temperature (15°-25° C.) and the excess thionyl chloride is then evaporated. The residue is taken up in dimethylformainde (DMF) and the latter is then evaporated. Finally, the residue is taken up in 500 ml of DMF (it is not necessary to isolate the 3,4-methylenedioxybenzyl chloride thus obtained).

Workup

customthe excess thionyl chloride is then evaporated
customthe latter is then evaporated

Sources & evidence

ORD record: ord-6894a54152924af49879deb8373082ee
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04128656

Reaction notes

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