Ethanol → Benzoic acid, 2-chloro-4-methyl-, ethyl ester

HRID 450492

Reaction equation

HRID 450492 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#N.S(=O)(=O)(O)O.[OH-:16].[Na+].[CH2:18]([OH:20])[CH3:19]>>[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]([O:20][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 3194752-Chloro-4-methylbenzonitrile

Product 1

HCID 14459377Benzoic acid, 2-chloro-4-methyl-, ethyl esterYield 45%

Procedure

A mixture of 2-chloro-4-methylbenzonitrile (5.5 g, 36.28 mmol), conc. sulfuric acid (30 mL) and ethanol (30 mL) was heated under reflux for 22 hr. The reaction mixture was ice-cooled, and neutralized with 8N aqueous sodium hydroxide solution, and ethanol was evaporated. The residue was extracted with ethyl acetate, and the extract was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was diluted with ethyl acetate-hexane (1:10, 120 mL). The insoluble material was filtered off, and the filtrate was under reduced pressure and concentrated to give the title compound (3.23 g, 45%) as a pale-brown liquid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 22 hr
  3. temperaturecooled
  4. customwas evaporated
  5. extractionThe residue was extracted with ethyl acetate
  6. washthe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionThe residue was diluted with ethyl acetate-hexane (1:10, 120 mL)
  10. filtrationThe insoluble material was filtered off
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-5381ed1223bf4979aa1c762f6bc98d93
Source dataset
uspto-grants-2013_07
Patent number
US08486965B2

Linked notes

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