Thionyl Chloride → 1-(Chloromethyl)-7-methoxynaphthalene

HRID 2090564Notes

Reaction equation

HRID 2090564 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13]O)=[CH:5][CH:4]=1.S(Cl)([Cl:17])=O>ClCCl.C(OCC)(=O)C>[Cl:17][CH2:13][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 154530791-Hydroxymethyl-7-Methoxynaphthalene

Product 1

HCID 199673051-(Chloromethyl)-7-methoxynaphthaleneYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound obtained in Step A (100 g) in dichloromethane (5 ml/g) there are added 2 equivalents of thionyl chloride (126.35 g). The mixture is heated to reflux and maintained at reflux for 2 hours. After returning to ambient temperature, the solvent is evaporated off under reduced pressure. The oil obtained is taken up in ethyl acetate and washed with water and then with saturated NaCl solution. The solvent is evaporated off under reduced pressure and the crude product is purified by passing over a pad of silica (eluant: heptane). The title compound is obtained in the form of a yellow solid in a yield of 84%.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux for 2 hours
  5. customAfter returning to ambient temperature
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe oil obtained
  8. washwashed with water
  9. customThe solvent is evaporated off under reduced pressure
  10. customthe crude product is purified

Sources & evidence

ORD record
ord-f2d54c71b22c496a838aee1a9549836d
Source dataset
uspto-grants-2013_05
Patent number
US08436206B2

Reaction notes

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