Methanol → Methyl 3-(chloromethyl)benzoate

HRID 1858291Notes

Reaction equation

HRID 1858291 reaction equation
S(Cl)(Cl)=O.[Cl:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].[CH3:16]O>>[CH3:16][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[C:7]([CH2:6][Cl:5])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2417523-(Chloromethyl)benzoic acid

Product 1

HCID 3248988Methyl 3-(chloromethyl)benzoateYield 88%

Procedure

650 μl (8.8 mmol) of thionyl chloride was added dropwise to a stirred solution of 1 g (5.8 mmol) of 3-(chloromethyl)benzoic acid in 40 ml of methanol at 0° C. under a nitrogen atmosphere, then stirred at room temperature overnight. The solvent was evaporated, the residue dissolved in dichloromethane (30 ml), washed with saturated aqueous sodium bicarbonate (2×40 ml), brine (40 ml), dried over magnesium sulfate, filtered and evaporated to give 0.94 g (88%) of methyl-3-(chloromethyl)benzoate as a colorless mobile liquid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane (30 ml)
  3. washwashed with saturated aqueous sodium bicarbonate (2×40 ml), brine (40 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0e559c0a5f7740bbafbc5b1d5a665e23
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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