Sulfuric Acid → 2-Chloro-6-ethylbenzaldehyde

HRID 254546Notes

Reaction equation

HRID 254546 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-6e18d6214eca4f2a90d41ad4c22c7fee
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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