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

HRID 1377164Notes

Reaction equation

HRID 1377164 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.C(C1C=CC=CC=1C=C)=C>CCOCC>[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

5

Reactant 3

HCID 10322Piperonyl alcoholHCID 24386Thionyl ChlorideHCID 666661,2-Diethenylbenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

15.04 ml of thionyl chloride are added dropwise, at 0° C., over the space of 25 min and under argon, to 10.82 g of 3,4-methylenedioxybenzyl alcohol (Fluka, Buchs, Switzerland) and 48 g of diisopropylaminomethylpolystyrene (polyhunig base: polystyrene crosslinked with 2% divinylbenzene, diisopropylaminomethylated; Fluka, Buchs, Switzerland) in 200 ml of abs. ether. After having been stirred at 0° C. for a further 1.5 h, the mixture is filtered with suction and the filtrate is concentrated on a RE and then under HV. The residue is purified by chromatography on silica gel (eluent: C), and the title compound thus obtained. TLC Rf (hexane:ethyl acetate, 4:1)=0.47; 1H-NMR (200 MHz, CDCl3): 6.95-6.7(m, 3H), 5.97(s, 2H), 4.53(s, 2H).

Workup

  1. filtrationthe mixture is filtered with suction
  2. concentrationthe filtrate is concentrated on a RE and then under HV
  3. customThe residue is purified by chromatography on silica gel (eluent: C)

Sources & evidence

ORD record
ord-69d6b927a6b04426a6ba05302df673f9
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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