Water → HCID 22114930, compound

HRID 1276134Notes

Reaction equation

HRID 1276134 reaction equation
P(=O)(O)(O)O.O.[Cl:7][C:8]1[C:17]([CH:18]=[CH:19][O:20]C)=[C:16]([Cl:22])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]>O1CCOCC1>[Cl:7][C:8]1[C:17]([CH2:18][CH:19]=[O:20])=[C:16]([Cl:22])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 54409558HCID 54409558, compound

Product 1

HCID 22114930HCID 22114930, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6 ml of 85% strength phosphoric acid and 6 ml of H2O were added dropwise to 2.6 g (10 mmol) of methyl 2,4-dichloro-3-(2-methoxyethen-1-yl)benzoate in 80 ml of dioxane. The mixture was heated under reflux for 12 hours and then stirred at room temperature for 12 hours. The solvent was removed and the residue was taken up in ethyl acetate, washed with 10% strength sodium bicarbonate solution, dried and concentrated. The residue was chromatographed over silica gel (eluent: cyclohexane:ethyl acetate=9:1). 1.4 g (57% of theory) of methyl 2,4-dichloro-3-(2-oxoeth-1-yl)benzoate were obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. customThe solvent was removed
  4. washwashed with 10% strength sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel (eluent: cyclohexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-ef61a9efae514e619f36102cdf8ca504
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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