Thionyl Chloride → 4-Chloro-6-(chloromethyl)-1,3-dioxaindane

HRID 705702Notes

Reaction equation

HRID 705702 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH2:11]O)[CH:3]=1.O=S(Cl)[Cl:15]>ClCCl>[Cl:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH2:11][Cl:15])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 4962440(7-Chloro-1,3-dioxaindan-5-yl)methanol

Product 1

HCID 162270934-Chloro-6-(chloromethyl)-1,3-dioxaindaneYield 218.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (7-chloro-1,3-benzodioxol-5-yl)methanol (34.5 g, 0.185 mol) and SOCl2 (5.0 mL, 67 mmol) in dichloromethane (200 mL) was stirred at room temperature for 1 h and was then poured into ice water. The organic layer was separated and the aqueous phase was extracted with dichloromethane (3×150 mL). The combined extracts were washed with water and aqueous NaHCO3 solution, dried over Na2SO4 and evaporated under reduced pressure to afford the title compound (30.0 g; 80%), which was directly used in the next step.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with dichloromethane (3×150 mL)
  3. washThe combined extracts were washed with water and aqueous NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-349f4589ea6849c9b8c705f207c52054
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

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