Triethylamine → 1,3-Benzodioxole, 5-(chloromethyl)-
Reaction equation
[CH2:1](O)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.C(N(CC)CC)C.S(Cl)([Cl:21])=O>C1C=CC=CC=1>[Cl:21][CH2:1][C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Piperonyl alcohol (10 g, 65.7 mmol) was dissolved in benzene. Triethylamine (11 ml, 78.8 mmol) and thionyl chloride (11 ml, 131.4 mmol) were added dropwise thereto and was stirred for 24 hours at 0° C. The reaction mixture was extracted with sodium bicarbonate and ethyl acetate, the organic layer was separated, and dried over anhydrous magnesium sulfate to obtain 5-chloromethyl benzo[1,3]dioxol (11.2 g, yield 100%).
Workup
- extractionThe reaction mixture was extracted with sodium bicarbonate and ethyl acetate
- customthe organic layer was separated
- dry with materialdried over anhydrous magnesium sulfate
Sources & evidence
- ORD record
- ord-d083df6e630e4365a26adb042fc2f702
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741323B2
Reaction notes
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