3-(2,2-Dimethylpropyl)-1-cyclobutene-1-carboxylic acid → 3-(2,2-Dimethylpropyl)cyclobutane-1-carboxylic acid

HRID 1912066Notes

Reaction equation

HRID 1912066 reaction equation
[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH:4]1[CH2:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5]1>[Rh].O1CCCC1>[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH:4]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5]1

Participants

4

Reactant 1

HCID 866750383-(2,2-Dimethylpropyl)-1-cyclobutene-1-carboxylic acid

Product 1

HCID 866750393-(2,2-Dimethylpropyl)cyclobutane-1-carboxylic acidYield 106.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(2,2-Dimethylpropyl)-1-cyclobutenecarboxylic acid (163 g) and tetrahydrofuran (1300 mL) were mixed. After an addition of 5 w/w % rhodium on activated carbon (8.2 g) to the mixture, the mixture was stirred at RT for 35 hr under hydrogen atmosphere (1 atm). The 5 w/w % rhodium on activated carbon was filtered off and the filtrate was concentrated in vacuo to give the title compound (175.56 g) as a crude product.

Workup

  1. filtrationThe 5 w/w % rhodium on activated carbon was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-00ef334750cb43a59357434ae0c284cc
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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