1-Methyl-1,4-cyclohexadiene → HCID 86720824, compound

HRID 877323Notes

Reaction equation

HRID 877323 reaction equation
CC1CC=CCC=1.[CH2:8]([O:10][CH:11]([O:24][CH2:25][CH3:26])[C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=1)[CH3:9]>[Pd].C(O)C>[CH2:25]([O:24][CH:11]([O:10][CH2:8][CH3:9])[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=1)[CH3:26]

Participants

5

Reactant 2

HCID 780061-Methyl-1,4-cyclohexadieneHCID 86720825HCID 86720825, compound

Product 1

HCID 86720824HCID 86720824, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

1-Methyl-1,4-cyclohexadiene (10.0 mL, 89 mmol) was added to a suspension of (E)-methyl 3-(4-(diethoxymethyl)phenyl)acrylate (2.41 g, 9.13 mmol) and 10% palladium on carbon (2.4 g) in ethanol (40 mL). The reaction mixture was heated at 60° C. for 1.5 hours. The reaction mixture was filtered through celite and the filter cake washed with further ethanol. The solvent was evaporated at reduced pressure to afford the title compound (2.15 g, 89%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe filter cake washed with further ethanol
  3. customThe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-758e6f90e1644e4ba0b8b2449637a9e6
Source dataset
uspto-grants-2015_03
Patent number
US08987299B2

Reaction notes

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