Thionyl Chloride → 4-(Chloromethyl)-2-methoxy-1-methylbenzene

HRID 2368910Notes

Reaction equation

HRID 2368910 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10]O)[CH:6]=[CH:7][C:8]=1[CH3:9].O=S(Cl)[Cl:14]>C(Cl)Cl>[Cl:14][CH2:10][C:5]1[CH:6]=[CH:7][C:8]([CH3:9])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11744818(3-methoxy-4-methylphenyl)methanol

Product 1

HCID 116152544-(Chloromethyl)-2-methoxy-1-methylbenzeneYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-methoxy-4-methylphenyl)methanol (2.0 g, 13.0 mmol) in dry DCM (20 mL) at 0° C., SOCl2 (3.1 g, 26.0 mmol) was added slowly. The resulting solution was stirred at room temperature for 0.5 h. The mixture was evaporated, and the residue was dissolved in DCM (20 mL). The mixture was washed with saturated NaHCO3 (3×10 mL), dried over Na2SO4 and evaporated to give the title compound as brown oil (2.1 g).

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in DCM (20 mL)
  3. washThe mixture was washed with saturated NaHCO3 (3×10 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-9b45fe4982e74f12bf4536fe8cc6b919
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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