Ethanol → Ethyl 5-chloro-2-methylbenzoate

HRID 1269518Notes

Reaction equation

HRID 1269518 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH2:17][CH3:18])=[O:8]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 820095-Chloro-2-methylbenzoic acid

Product 1

HCID 21269135Ethyl 5-chloro-2-methylbenzoate

Procedure

5-chloro-2-methylbenzoic acid (5.04 g, 29.5 mmol) was dissolved in 100 mL ethanol in a 250 mL round bottom flask fitted with a water condenser. 0.5 mL concentrated sulfuric acid was added and the solution heated to reflux. The solution was heated for 48 h and cooled to ambient temperature. The ethanol was removed under reduced pressure. The resultant oil was taken up in 300 mL diethyl ether and washed with saturated aqueous sodium bicarbonate (2×300 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to yield 5.12 (87%) of ethyl 5-chloro-2-methylbenzoate as a clear oil.

Workup

  1. customfitted with a water condenser
  2. temperaturethe solution heated to reflux
  3. temperatureThe solution was heated for 48 h
  4. customThe ethanol was removed under reduced pressure
  5. washwashed with saturated aqueous sodium bicarbonate (2×300 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1b94d6512874838a504e3655f49e08a
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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