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

HRID 1717642Notes

Reaction equation

HRID 1717642 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.O=S(Cl)[Cl:14]>C1C=CC=CC=1>[Cl:14][CH2:1][C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 10322Piperonyl alcoholHCID 24386Thionyl Chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Piperonyl alcohol (45.64 g, 300 mmol) was dissolved in 340 ml of dry benzene, and SOCl2 (37 ml) was added dropwise with stirring. The solution was refluxed for 1 h, cooled and evaporated on the rotary evaporator (bath temperature less than 50° C.!). The resulting dark green residue was used without further purification.

Workup

  1. temperatureThe solution was refluxed for 1 h
  2. temperaturecooled
  3. customevaporated on the rotary evaporator (bath temperature less than 50° C.!)
  4. customThe resulting dark green residue was used without further purification

Sources & evidence

ORD record
ord-719f2699380f42cab4fc60c57c2d5323
Source dataset
uspto-grants-2010_09
Patent number
US07803887B2

Reaction notes

Loading…