Thionyl Chloride → 2-(Chloromethyl)-6-methoxynaphthalene

HRID 594322Notes

Reaction equation

HRID 594322 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:13]O)[CH:7]=[CH:6]2.O=S(Cl)[Cl:17]>C(Cl)Cl>[Cl:17][CH2:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10012701(6-methoxynaphthalen-2-yl)methanol

Product 1

HCID 133842572-(Chloromethyl)-6-methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) mixture of (6-methoxynaphthalen-2-yl)methanol (90 mg; 0.48 mmol) in anh. DCM (2 ml) was treated dropwise with SOCl2 (89 mg; 0.75 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 17 h. The volatiles were removed under reduced pressure, and the solid residue was triturated with Et2O. Filtration afforded 2-(chloromethyl)-6-methoxynaphthalene which was directly used for the next reaction. LC-MS (conditions E): tR=0.75 min.; no ionisation.

Workup

  1. temperatureA cooled
  2. customThe volatiles were removed under reduced pressure
  3. customthe solid residue was triturated with Et2O
  4. filtrationFiltration

Sources & evidence

ORD record
ord-ec24be16e91f4739b50b89f355dc10f7
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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