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

HRID 1522863Notes

Reaction equation

HRID 1522863 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-d8f367b6865d4641acc9fece2c0f9ffa
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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