Ethanol → Ethyl 4-bromo-2-methylbenzoate

HRID 2102919Notes

Reaction equation

HRID 2102919 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.OS(O)(=O)=O.[CH3:17][CH2:18]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:17][CH3:18])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22616358Ethyl 4-bromo-2-methylbenzoate

Procedure

4-bromo-2-methylbenzoic acid (10 g, 46.5 mmol) was dissolved in 200 mL EtOH, 5 mL conc H2SO4 was added and the mixture was refluxed for 18 h. The reaction volume was reduced in vacuo to 50 mL, and neutralized to pH 7 with satd. aqueous NaHCO3 and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and the filtrate was concentrated to give the product (6.5 g) as an oil.

Workup

  1. temperaturethe mixture was refluxed for 18 h
  2. extractionaqueous NaHCO3 and extracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c07a86d5d7fe48b293ce826736e288eb
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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