(E)-3-[4-(1,1-dimethylethyl)phenyl]-2-propenoic acid phenylmethyl ester → 3-(4-Tert-butylphenyl)propanoic acid

HRID 653952Notes

Reaction equation

HRID 653952 reaction equation
C1(C[O:8][C:9](=[O:22])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)C=CC=CC=1>[Pd].CCO>[CH3:21][C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][C:9]([OH:22])=[O:8])=[CH:17][CH:16]=1)([CH3:19])[CH3:20]

Participants

4

Reactant 1

HCID 67918730(E)-3-[4-(1,1-dimethylethyl)phenyl]-2-propenoic acid phenylmethyl ester

Product 1

HCID 49621733-(4-Tert-butylphenyl)propanoic acidYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirring solution of (E)-3-[4-(1,1-dimethylethyl)phenyl]-2-propenoic acid phenylmethyl ester (2.04 g, 6.93 mmol) in 136 mL of abs. EtOH in the presence of 377 mg of 10% Pd/C was hydrogenated at room temperature at atmospheric pressure. After removing the catalyst by filtration through a pad of celite, the filtrate was concentrated to give 4-(1,1-dimethylethyl)benzenepropanoic acid, (1.39 g, 6.74 mmol) in 97% yield, m.p. 110°-113° C.

Workup

  1. customwas hydrogenated at room temperature at atmospheric pressure
  2. customAfter removing the catalyst
  3. filtrationby filtration through a pad of celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-da28d780ee55448e8c43a08a0e7247b8
Source dataset
uspto-grants-1992_07
Patent number
US05128448

Reaction notes

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