3-Methyl-2-(2-methyl-1-propenyl)benzoic acid → 2-Isobutyl-3-methylbenzoic acid

HRID 1047903Notes

Reaction equation

HRID 1047903 reaction equation
[CH3:1][C:2]1[C:3]([CH:11]=[C:12]([CH3:14])[CH3:13])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]>CO.[Pd]>[CH2:11]([C:3]1[C:2]([CH3:1])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 1

HCID 593140863-Methyl-2-(2-methyl-1-propenyl)benzoic acid

Product 1

HCID 593142962-Isobutyl-3-methylbenzoic acidYield 91.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the 3-methyl-2-(2-methyl-1-propenyl)benzoic acid (291) (2 g, 10.5 mmol) in MeOH (40 mL) is hydrogenated using 10% palladium/carbon catalyst at 40 bar/30° C. using the Thales nanotechnology H-cube for 48 h. The MeOH is concentrated in vacuo to give the product as colorless oil (1.85 g, 90%).

Workup

  1. customat 40 bar/30° C.
  2. customfor 48 h
  3. concentrationThe MeOH is concentrated in vacuo

Sources & evidence

ORD record
ord-679da73c132146bcb4373914592281fa
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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