Methanol → Methyl 3-chloro-2-methylbenzoate

HRID 1958009Notes

Reaction equation

HRID 1958009 reaction equation
[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[OH-].[Na+].[CH3:19]O>CCOCC>[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:19])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 820103-Chloro-2-methylbenzoic acid

Product 1

HCID 5077673Methyl 3-chloro-2-methylbenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-chloro-2-methylbenzoic acid (1 g, 5.86 mmol) and sulfuric acid (0.312 mL, 5.86 mmol) in Methanol (5 mL) was charged into a round bottom flask. The reaction was stirred at reflux overnight and cooled to RT. 1N NaOH was added to adjust pH to 7. The mixture was diluted with ether, which was washed with brine. The organic layer was dried over MgSO4 and the solvent was removed to afford 1.07 g of crude product (99%). 1H NMR (400 MHz, CDCl3) δppm 7.71 (m, 1H), 7.52 (m, 1H), 7.20 (m, 1H), 3.92 (s, 3H). 2.62 (s, 3H).

Workup

  1. temperatureat reflux overnight
  2. washwas washed with brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-93c1abe6647a4cb2b89dc9c1a1109697
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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