2-Propenoic acid, 3-(4-chlorophenyl)- → beta-(p-Chlorophenyl)propionic acid

HRID 1978286Notes

Reaction equation

HRID 1978286 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1>C1COCC1.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 153712-Propenoic acid, 3-(4-chlorophenyl)-

Product 1

HCID 123137beta-(p-Chlorophenyl)propionic acidYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.80 g (10 mmol) of 4-chlorocinnamic acid in 50 mL of THF was added Pd/C (1.04 g, 5% w/w) and the solution was stirred under a hydrogen atmosphere until no further H2 take-up was observed (˜1 h). The solution was filtered through Celite and the solvent removed under reduced pressure to yield 1.82 g (9.8 mmol, 98%) of a white solid: mp. 103-105° C.; 1H NMR (DMSO-d6) δ2.51 (t, 2H, β-CH2), 2.79 (t, 2H, α-CH2), 7.28 (dd, 4H, aromatic CH's), 12.12 (s, 1H, COOH); MS (EI, calculated for C9H9ClO2, 184.0291) m/e 184.0288 (M+).

Workup

  1. custom(˜1 h)
  2. filtrationThe solution was filtered through Celite
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f791bc799ab0483e96a7380b13e133a9
Source dataset
uspto-grants-2001_05
Patent number
US06235929B1

Reaction notes

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