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

HRID 889677Notes

Reaction equation

HRID 889677 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-cd57744f3516438d81b2f6fb6c4900ce
Source dataset
uspto-grants-2012_08
Patent number
US08252951B2

Reaction notes

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