Thionyl Chloride → 6-(Chloromethyl)-2,3-dihydro-1,4-benzodioxine

HRID 468308Notes

Reaction equation

HRID 468308 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11]O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.O=S(Cl)[Cl:15]>>[Cl:15][CH2:11][C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27761742,3-Dihydro-1,4-benzodioxin-6-methanol

Product 1

HCID 52302876-(Chloromethyl)-2,3-dihydro-1,4-benzodioxineYield 88%

Procedure

A mixture of (2,3-dihydro-benzo[1,4]dioxin-6-yl)methanol (10.6 g) in SOCl2 (10 mL) was stirred at room temperature for 10 min and then poured into ice-water. The organic layer was separated and the aqueous phase was extracted with dichloromethane (50 mL×3). The combined organic layers were washed with NaHCO3 (sat solution), water and brine, dried over Na2SO4 and concentrated to dryness to obtain 6-chloromethyl-2,3-dihydro-benzo[1,4]dioxine (12 g, 88% over two steps), which was used directly in next step.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with dichloromethane (50 mL×3)
  3. washThe combined organic layers were washed with NaHCO3 (sat solution), water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-83040c44f253401c8fd02be389c1f647
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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