Methyl 4-Chloro-2-(3-methoxy-3-oxo-1-propenyl)-benzoate → Methyl 4-chloro-2-(3-methoxy-3-oxopropyl)benzoate

HRID 1282407Notes

Reaction equation

HRID 1282407 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH:12]=[CH:13][C:14]([O:16][CH3:17])=[O:15])[CH:3]=1.[H][H]>CO.[Pd]>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:3]=1

Participants

5

Reactant 2

HCID 69978143Methyl 4-Chloro-2-(3-methoxy-3-oxo-1-propenyl)-benzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 18424532Methyl 4-chloro-2-(3-methoxy-3-oxopropyl)benzoateYield 79.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

26.1 g of the methyl 4-chloro-2-(3-methoxy-3-oxo-1-propenyl)-benzoate prepared according to Example 1 are taken up in 300 ml of methanol and transferred into an autoclave and then hydrogenated at 30° C. and a hydrogen pressure of 30 bar for 5 h, until the theoretical amount of hydrogen has been taken up. The substance contains the palladium catalyst required for the Heck coupling, so that separate addition of a hydrogenation catalyst can be dispensed with. The pressure is reduced to 1 bar, and insoluble components are then filtered off. Solvent is then removed under reduced pressure until the hydrogenation product precipitates. Recrystallization gives 21 g of methyl 4-chloro-2-(3-methoxy-3-oxo-1-propanyl)-benzoate.

Workup

  1. customhydrogenated at 30° C.
  2. customso that separate
  3. additionaddition of a hydrogenation catalyst
  4. filtrationare then filtered off
  5. customSolvent is then removed under reduced pressure until the hydrogenation product
  6. customprecipitates
  7. customRecrystallization

Sources & evidence

ORD record
ord-045bc2c809c249599cde5dbd30c52389
Source dataset
uspto-grants-2002_09
Patent number
US06455725B1

Reaction notes

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