Methanol → Methyl 2-chloro-3-methylbenzoate

HRID 2190451Notes

Reaction equation

HRID 2190451 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1398792-Chloro-3-methylbenzoic acid

Product 1

HCID 25067288Methyl 2-chloro-3-methylbenzoateYield 66%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-3-methylbenzoic acid (25.0 g, 0.146 mol), concentrated sulfuric acid (2 mL) and methanol (160 mL) was stirred at 80° C. for 3 hr. The reaction mixture was concentrated, diluted with ethyl acetate and neutralized with 8N aqueous sodium hydroxide solution. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and passed through a pad filled with basic silica gel for filtration. The solvent was concentrated under reduced pressure to give the title compound (18.0 g, 66%) as a pale-orange oil. The obtained compound was used in the next reaction without a further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate and neutralized with 8N aqueous sodium hydroxide solution
  3. customThe organic layer was separated
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additionfilled with basic silica gel for filtration
  7. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7c9cac8a9d854d338d279f589751d830
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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