Methyl 4-tert-butyl-3-(prop-1-en-2-yl)benzoate → Methyl 4-tert-butyl-3-isopropylbenzoate

HRID 1675254Notes

Reaction equation

HRID 1675254 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[C:15]([CH3:17])=[CH2:16])([CH3:4])([CH3:3])[CH3:2]>CCO.CCOC(C)=O.[OH-].[OH-].[Pd+2]>[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH:15]([CH3:17])[CH3:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59300653Methyl 4-tert-butyl-3-(prop-1-en-2-yl)benzoate

Product 1

HCID 59300556Methyl 4-tert-butyl-3-isopropylbenzoateYield 86%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To the ester 26.2 (167 mg, 0.72 mmol) in EtOH/EtOAc (1/1, v/v, 3.00 mL), was added Pd(OH)2/C (10 mg). The mixture was placed under an atmosphere of hydrogen and stirred for 8 days. The resulting mixture was filtered through Celite and concentrated in vacuo to give a clear oil (145 mg, 86%). The crude product (26.3) was used in the next step without further purification.

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1731211647ca475c9b915096fba15977
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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