Thionyl Chloride → 2-Chloromethyl-5,6,7-trimethoxynaphthalene

HRID 720303Notes

Reaction equation

HRID 720303 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:17][CH3:18])=[C:8]([O:15][CH3:16])[C:9]=2[O:13][CH3:14])[CH:4]=1.S(Cl)([Cl:21])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:21][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:17][CH3:18])=[C:8]([O:15][CH3:16])[C:9]=2[O:13][CH3:14])[CH:4]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 218915782-Hydroxymethyl-5,6,7-trimethoxynaphthalene

Product 1

HCID 218916422-Chloromethyl-5,6,7-trimethoxynaphthalene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Hydroxymethyl-5,6,7-trimethoxynaphthalene (781 mg) was dissolved in chloroform (6 mL), and thionyl chloride (561 mL) was added dropwise to the solution. After stirring at room temperature for 5 hours, the reaction mixture was poured into ice water, and sodium hydrogencarbonate was added to adjust the pH of the reaction mixture to 8 to conduct extraction with ethyl acetate. The resultant organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain the title compound.

Workup

  1. additionwas added
  2. extractionextraction with ethyl acetate
  3. washThe resultant organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55f8372451644e1b8dd629ed599d8b66
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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