Benzenepropanoic acid, alpha-(phenylmethyl)- → Bis-(cyclohexylmethyl)acetic acid

HRID 976051Notes

Reaction equation

HRID 976051 reaction equation
[CH2:1]([CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O>[CH:2]1([CH2:1][CH:8]([CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([OH:11])=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 1

HCID 64800Benzenepropanoic acid, alpha-(phenylmethyl)-

Product 1

HCID 19968574Bis-(cyclohexylmethyl)acetic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.0 g (12.5 mmol) of dibenzyl acetic acid in 100 mL of HOAc was treated with 0.5 g PrO2 and reduced with H2 at 25° C., 50 psi. When the required amount of H2 had been taken up, the mixture was filtered and the solvent removed under reduced pressure. Hexane was added and the solvent removed again leaving 3.1 g (98.4% yield) of the product as an oil which crystallized on standing, mp 67°-69° C. The structure was confirmed by NMR and mass spectroscopy.

Workup

  1. customreduced with H2 at 25° C.
  2. filtrationthe mixture was filtered
  3. customthe solvent removed under reduced pressure
  4. additionHexane was added
  5. customthe solvent removed again

Sources & evidence

ORD record
ord-cf1bdad392564fa39ba1a4fbddc79bf6
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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