Sulfuric Acid → 2-Chloro-6-ethylbenzaldehyde

HRID 1694805Notes

Reaction equation

HRID 1694805 reaction equation
C(/N=[CH:6]/[C:7]1[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:15])CCC.S(=O)(=O)(O)[OH:17]>O.C(OCC)(=O)C>[Cl:15][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([CH2:13][CH3:14])[C:7]=1[CH:6]=[O:17]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 178448975HCID 178448975, compound

Product 1

HCID 226137462-Chloro-6-ethylbenzaldehydeYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 19.7 g (88.1 mmol) butyl-[1-(2-chloro-6-ethyl-phenyl)-meth-(E)-ylidene]-amine in 70 ml water at 0° C. was added dropwise 18.9 ml concentrated sulphuric acid. The mixture was then heated at reflux for 90 min before being cooled to room temperature and diluted with ethyl acetate. The mixture was then washed sequentially with water, saturated aqueous sodium bicarbonate solution, and saturated brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate/heptane 1:30) to afford 11.4 g (77%) of the title compound as a yellow oil. 1H-NMR (CDCl3): 1.22 (3H, t, CH3), 2.97 (2H, q, CH2), 7.20 (1H, d, ArH), 7.30 (1H, d, ArH), 7.39 (1H, dd, ArH), 10.65 (1H, s, CHO).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 90 min
  3. washThe mixture was then washed sequentially with water, saturated aqueous sodium bicarbonate solution, and saturated brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane 1:30)

Sources & evidence

ORD record
ord-b41f0e2f446f4d4db6bd5afbcd86beb4
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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