Methanol → Methyl 2-chloro-5-methylbenzoate

HRID 1435763Notes

Reaction equation

HRID 1435763 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)(=O)C(Cl)=O.CO>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 2404302-Chloro-5-methylbenzoic Acid

Product 1

HCID 57362636Methyl 2-chloro-5-methylbenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-chloro-5-methyl-benzoic acid (3.0 g, 17.6 mmol) in dichloromethane (50 ml) was added a solution of oxalyl chloride in dichloromethane (2 M, 10 ml, 20 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 1 hour, methanol (20 ml) was added. After stirring for 3 hours, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 ml) and saturated aqueous potassium carbonate solution (100 ml). The organic layer was concentrated under reduced pressure to provide methyl 2-chloro-5-methyl-benzoate (3.2 g, 100% yield).

Workup

  1. stirringAfter stirring for 3 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (200 ml) and saturated aqueous potassium carbonate solution (100 ml)
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-59a6e2f0b4c64ad0acb1e078128780ff
Source dataset
uspto-grants-2009_11
Patent number
US07618968B2

Reaction notes

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