Ethyl 3,3-bis(3-fluorophenyl)acrylate → Ethyl 3,3-bis(3-fluorophenyl)propionate

HRID 1167248Notes

Reaction equation

HRID 1167248 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1>C(O)C.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22015772Ethyl 3,3-bis(3-fluorophenyl)acrylate

Product 1

HCID 22996571Ethyl 3,3-bis(3-fluorophenyl)propionateYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3,3-bis(3-fluorophenyl)acrylate (38.81 g, 134.8 mmol) in absolute ethanol (300 mL) was hydrogenated in the presence of palladium hydroxide on carbon (5 g wet, Degussa type) at 60 p.s.i. H2 for 30 min at ambient temperature. After this time the reaction was filtered and concentrated to afford 39.08 g (100%) of the title compound as a clear, colorless oil. GC/EI-MS analysis gave a single component: Rt=6.21 min, m/z (rel.int.) 290 (M+,6), 262 (1), 244 (5), 216 (100), 203 (67), 201 (48), 183 (63), 101 (41), 96 (17), and 75 (25).

Workup

  1. filtrationAfter this time the reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e8674c39b420443191c5f06c4eb400d5
Source dataset
uspto-grants-2003_09
Patent number
US06617358B1

Reaction notes

Loading…