Acetone → 157766-09-1

HRID 1377165Notes

Reaction equation

HRID 1377165 reaction equation
[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][C:3]=2[O:2]1.CC(C)=O.[I-:16].[Na+]>CCOCC>[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH2:6][I:16])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 887131,3-Benzodioxole, 5-(chloromethyl)-

Product 1

HCID 11086556157766-09-1

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

11.65 g 3,4-methylenedioxybenzyl chloride in 128 ml of abs. acetone are treated with 49.7 g of sodium iodide, and this mixture is stirred at RT for 2.5 h under argon and while excluding light. The reaction mixture is diluted with 1.5 l of ether, and this mixture is washed with 10% sodium thiosulfate solution (600 ml) and saline. The title compound is obtained after drying over sodium sulfate and removing the solvent. It is recrystallized from ether/hexane. m.p.: 51° C. TLC Rf (hexane:ethyl acetate, 4:1)=0.43. 1H-NMR (360 MHz, CDCl3): 6.93-6.77(m, 2H), 6.77-6.64(m,1H), 5.95(s, 2H), 4.44 (s,2H).

Workup

  1. washthis mixture is washed with 10% sodium thiosulfate solution (600 ml) and saline

Sources & evidence

ORD record
ord-23d15350930a4a2e9f89e15ae1530b5e
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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