Ethanol → HCID 10922417, compound

HRID 368948Notes

Reaction equation

HRID 368948 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])=[CH:9][C:10]=1[Cl:11])[C:5]([O:7][CH2:18][CH3:19])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 110090583,4-dichloro-6-methylbenzoic acid

Product 1

HCID 10922417HCID 10922417, compoundYield 97%

Procedure

92.1 g (421 mmol) of the 3,4-dichloro-6-methylbenzoic acid obtained in the above step (2) was dissolved in 550 ml of ethanol as both an esterifying agent and a solvent, 20 ml of concentrated sulfuric acid as an acid catalyst was added, and the mixture was refluxed under heat for 7 hours. The ethanol was distilled off under reduced pressure, ice water was added, and the mixture was extracted with ethyl acetate twice. The resultant organic layer was consecutively washed with a sodium carbonate aqueous solution and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 103.4 g (yield 97%) of ethyl 3,4-dichloro-6-methylbenzoate as a crude product.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat for 7 hours
  3. distillationThe ethanol was distilled off under reduced pressure, ice water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate twice
  6. washThe resultant organic layer was consecutively washed with a sodium carbonate aqueous solution and with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4001b3a8f85445a4bf1c82673892a190
Source dataset
uspto-grants-2000_10
Patent number
US06136755

Reaction notes

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