Ethyl γ-methyl-4-nitrobenzenebutanoate → HCID 12561714, compound

HRID 1085198Notes

Reaction equation

HRID 1085198 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 12561711Ethyl γ-methyl-4-nitrobenzenebutanoate

Product 1

HCID 12561714HCID 12561714, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 114 g of ethyl 4-(4-nitrophenyl)pentanoate, 170 ml of absolute ethanol and 2 g of 10% of palladium-on-charcoal was hydrogenated on a Paar shaker until consumption of hydrogen ceased. The catalyst was collected and the ethanol evaporated. The residue was partitioned between water and ether. The ether extract was washed with 5% of sodium bicarbonate solution and water, dried over anhydrous sodium sulfate, filtered and evaporated to give 85 g (86%) of product, bp 118°-122° C. (0.55-0.60 mm).

Workup

  1. customwas hydrogenated on a Paar shaker until consumption of hydrogen
  2. customThe catalyst was collected
  3. customthe ethanol evaporated
  4. customThe residue was partitioned between water and ether
  5. extractionThe ether extract
  6. washwas washed with 5% of sodium bicarbonate solution and water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-6d2c7af7e22746458aa4bab8c0b9d22b
Source dataset
uspto-grants-1991_04
Patent number
US05008285

Reaction notes

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