4-Phenylbutyric Acid → Cyclohexanebutanoic acid

HRID 978062Notes

Reaction equation

HRID 978062 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)(=O)C.[Pt]=O>[CH:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 47754-Phenylbutyric AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 75200Cyclohexanebutanoic acidYield 77%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

4-Phenylbutanoic acid prepared as described in Example 56, Part A was dissolved in glacial acetic acid (25 ml). Platinum oxide (0.1 g) was added and the solution was hydrogenated in the Paar shaker at up to 55 p.s.i. until hydrogen uptake ceased (6.5 hours). The catalyst was removed by filtration and the acetic acid was removed in vacuo. The product crystallized and was recrystallized from Et2O (20 ml) to give title compound (1.18 g, 77%), m.p. 85°-88° C.

Workup

  1. custom(6.5 hours)
  2. customThe catalyst was removed by filtration
  3. customthe acetic acid was removed in vacuo
  4. customThe product crystallized
  5. customwas recrystallized from Et2O (20 ml)

Sources & evidence

ORD record
ord-8412c792443a449aaf559fa51878da33
Source dataset
uspto-grants-1987_05
Patent number
US04663336

Reaction notes

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