3-Isobutyl-1-cyclobutenecarboxylic acid → cis-3-Isobutylcyclobutane carboxylic acid

HRID 1912043Notes

Reaction equation

HRID 1912043 reaction equation
[CH2:1]([CH:5]1[CH2:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6]1)[CH:2]([CH3:4])[CH3:3]>[Rh].O1CCCC1>[CH2:1]([CH:5]1[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[CH2:8]1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 866750313-Isobutyl-1-cyclobutenecarboxylic acid

Product 1

HCID 83635449cis-3-Isobutylcyclobutane carboxylic acidYield 70.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

3-Isobutyl-1-cyclobutenecarboxylic acid (188 g) and tetrahydrofuran (2000 mL) were mixed. To the mixture was added 5 w/w % rhodium on activated carbon (5.64 g). The resulting mixture was stirred at RT for 7 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 (134.06 g) as a crude product.

Workup

  1. filtrationwas filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a85d21ab2ffd4abcab37a2ea848017fd
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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