1,4-Benzodioxane-2-methanol → 2-(Chloromethyl)-2,3-dihydro-1,4-benzodioxin

HRID 370649

Reaction equation

HRID 370649 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH:7]1[O:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][CH2:8]1>>[Cl:3][CH2:6][CH:7]1[O:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][CH2:8]1

Participants

3

Reactant 2

HCID 193141,4-Benzodioxane-2-methanolHCID 24386Thionyl Chloride

Product 1

HCID 953202-(Chloromethyl)-2,3-dihydro-1,4-benzodioxin

Procedure

A mixture of thionyl chloride (36.0 g, 0.3 mol) and 2-hydroxymethyl-1,4-benzodioxan (25.0 g, 0.15 mol) was stirred and heated under reflux for 0.75 h. The reaction mixture was concentrated under reduced pressure, and the residue was distilled, to afford 2-chloromethyl-1,4-benzodioxan, b.p. 140°-146°/22 mm Hg.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 0.75 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-0ef3d80b0c1849b68cfb5df7905da678
Source dataset
uspto-grants-1985_07
Patent number
US04528195

Linked notes

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