4-Isobutylbenzoic acid → HCID 178445659, compound

HRID 528704Notes

Reaction equation

HRID 528704 reaction equation
[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[H][H]>C(O)(=O)C.[Pt](=O)=O>[CH2:1]([C@H:5]1[CH2:13][CH2:12][C@H:8]([C:9]([OH:11])=[O:10])[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 381114-Isobutylbenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 178445659HCID 178445659, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4-isobutylbenzoic acid (1.0 g, 5.6 mmol) in acetic acid (56 ml) was purged with argon. After addition of platinum(IV) oxide (0.38 g, 1.7 mmol) the reaction flask was filled with hydrogen gas. The reaction mixture was stirred under an atmosphere of hydrogen gas for 72 h at RT. The flask was purged with argon, and the catalyst was removed by filtration over Decalite. The filtrate was concentrated to dryness to give the title compound as a (7:3) cis/trans mixture. MS m/e: 183 ([M−H]−)

Workup

  1. customThe flask was purged with argon
  2. customthe catalyst was removed by filtration over Decalite
  3. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-26a56c138a304dd0a23b6ef138724901
Source dataset
uspto-grants-2016_05
Patent number
US09346824B2

Reaction notes

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