(Z)-methyl 4-(pent-2-en-2-yl)benzoate → Methyl 4-(pentan-2-yl)benzoate

HRID 2170491Notes

Reaction equation

HRID 2170491 reaction equation
[CH3:1]/[C:2](/[C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)=[CH:3]/[CH2:4][CH3:5].[H][H]>C1(C)CCC(C(C)C)C(O)C1.[Pd]>[CH3:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 89581156(Z)-methyl 4-(pent-2-en-2-yl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 76779858Methyl 4-(pentan-2-yl)benzoateYield 108.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1254MentholSolvent

Procedure

To a solution of (Z)-methyl 4-(pent-2-en-2-yl)benzoate (600 mg, 2.15 mmol) in menthol was added Palladium 10% on Carbon (340 mg, 0.3 mmol) and the mixture was hydrogenated at hydrogen gas pressure 4 atmosphere for 8 hours. The reaction mixture was filtered. The filtrate was evaporated and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=8:1) to get methyl 4-(pentan-2-yl)benzoate (480 mg, 80%). LRMS (M+H+) m/z: calcd 206.13. found 206.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customThe filtrate was evaporated
  3. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=8:1)

Sources & evidence

ORD record
ord-da65f2eb91b2467091354293d874c2ce
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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