Water → 2-Ethylhexyl 2-cyano-3,3,-diphenyl-propionate

HRID 2386100Notes

Reaction equation

HRID 2386100 reaction equation
[C:1]([C:3](=[C:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5])#[N:2].O.[3H][3H]>O1CCCC1.[Pd]>[C:1]([CH:3]([CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5])#[N:2]

Participants

6

Reactant 3

HCID 962WaterHCID 22571OctocryleneHCID 24824Tritium

Product 1

HCID 119611652-Ethylhexyl 2-cyano-3,3,-diphenyl-propionate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Ethylhexyl 2-cyano-3,3-diphenylacrylate (Eusolex® OCR; Merck) is dissolved in tetrahydrofuran (THF), and 5% Pd/C (56% water; Merck: Art. No. 275175) is added. The hydrogenation is subsequently carried out with hydrogen 3.0 at room temperature and atmospheric pressure. The catalyst is separated off by filtration. The filtrate is freed from solvent in vacuo, and the residue is washed. The organic phase is dried over sodium sulfate, and the solvent is removed in vacuo. The purification is carried out by filtration through silica gel, giving analytically pure product.

Workup

  1. addition275175) is added
  2. customat room temperature
  3. customThe catalyst is separated off by filtration
  4. washthe residue is washed
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customthe solvent is removed in vacuo
  7. customThe purification
  8. filtrationis carried out by filtration through silica gel
  9. customgiving analytically pure product

Sources & evidence

ORD record
ord-edea59ab6a7c41c59095a2c67fceec82
Source dataset
uspto-grants-2012_09
Patent number
US08268293B2

Reaction notes

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