Thionyl Chloride → 4-(Chloromethyl)benzo[d][1,3]dioxole

HRID 911322Notes

Reaction equation

HRID 911322 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10]O)[C:4]=2[O:3][CH2:2]1.S(Cl)([Cl:14])=O>>[Cl:14][CH2:10][C:9]1[C:4]2[O:3][CH2:2][O:1][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2776187(1,3-Dioxaindan-4-yl)methanol

Product 1

HCID 131037124-(Chloromethyl)benzo[d][1,3]dioxoleYield 91%

Procedure

Dissolve benzo[1,3]dioxol-4-yl-methanol (1.9 g, 12.5 mmol) in thionyl chloride (3 mL, 41.1 mmol) and reflux the reaction mixture for 1 h. Concentrate in vacuo to obtain the desired intermediate as a yellow oil (1.9 g, 91%) that was used without further purification. GC-MS m/z: 170 (M+).

Workup

  1. temperaturereflux the reaction mixture for 1 h
  2. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-81a9365f5c2349abb63d8f7366efadd0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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