Ethanol → 3-(4-Tert-butylphenyl)propanoic acid

HRID 1017145Notes

Reaction equation

HRID 1017145 reaction equation
C([C:5](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])(C)(C)C.O1[CH2:20][CH2:19][CH2:18]C1.[H][H].[CH2:23](O)C>[Pd]>[C:19]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH2:5][C:6]([OH:8])=[O:7])=[CH:15][CH:14]=1)([CH3:18])([CH3:20])[CH3:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 54357124t-Butylcinnamic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 49621733-(4-Tert-butylphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A 3 L autoclave was charged with wet t-butylcinnamic acid (248 g, 1.21 mol), tetrahydrofuran (1 L), and ethanol (1 L) and palladium on carbon (35 g). The reactor was shut and 90 psi of hydrogen pressure applied and the reactor held at room temperature overnight. The reaction was then transferred to a round bottom flask and concentrated to 200 mL. The formed crystals were decanted and washed with hexane to give 3-(4-t-butylphenyl)propionic acid (52.9 g after vacuum drying). A second crop from the filtrate yielded additional 3-(4-t-butylphenyl)propionic acid (65.8 g). 1HNMR (CD2Cl2, 500 MHz) δ9.85 (br s, 1H); 7.32 (d, J=8 Hz, 2H); 7.15 (d, JAB=8.5 Hz); 2.91 (t, J=8 Hz, 2H); 2.67 (t, J=8 Hz, 2H); 1.27 (s, 9H).

Workup

  1. customThe reaction was then transferred to a round bottom flask
  2. concentrationconcentrated to 200 mL
  3. customThe formed crystals were decanted
  4. washwashed with hexane

Sources & evidence

ORD record
ord-da68f309293546e392a33db547bf6e40
Source dataset
uspto-grants-2002_11
Patent number
US06479424B1

Reaction notes

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