Methanol → Methyl 3,5-dichlorobenzoate

HRID 1848277Notes

Reaction equation

HRID 1848277 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[C:10]([OH:12])=[O:11].[CH3:17]O>>[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[C:10]([O:12][CH3:17])=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 58113,5-Dichlorobenzoic acid

Product 1

HCID 76192Methyl 3,5-dichlorobenzoateYield 90.6%

Procedure

10 g of concentrated sulfuric acid was added to a methanol (120 g) solution of 50 g of 3,5-dichlorobenzoic acid, and the mixture was refluxed by heating for 5 hours. After cooling the reaction solution to room temperature, the solvent was distilled off under reduced pressure. The obtained residue was dissolved into 200 g of ethyl acetate, washed with water (200 g×2), then washed with a saturated aqueous solution of sodium bicarbonate, and further washed with water. After drying the organic phase over anhydrous magnesium sulfate, 48.6 g of the target product was obtained as a white solid by removing the solvent by distilling under reduced pressure.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 5 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe obtained residue was dissolved into 200 g of ethyl acetate
  5. washwashed with water (200 g×2)
  6. washwashed with a saturated aqueous solution of sodium bicarbonate
  7. washfurther washed with water
  8. dry with materialAfter drying the organic phase over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-686d0adfe7b444a7a082c7599170014c
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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