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

HRID 638253Notes

Reaction equation

HRID 638253 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% palladium-on-charcoal, was hydrogenated (Paar shaker) until consumption of hydrogen ceased. The catalyst was filtered and the ethanol evaporated. The residue was partitioned between water and ether. The ether extract was washed with 5% sodium bicarbonate and water. The ether extract was dried over anhydrous sodium sulfate, filtered and evaporated to give an oil. The oil was distilled 0.55-0.60 mm to give 85 g (86%) of product, b.p. 118°-122° C.

Workup

  1. customuntil consumption of hydrogen
  2. filtrationThe catalyst was filtered
  3. customthe ethanol evaporated
  4. customThe residue was partitioned between water and ether
  5. extractionThe ether extract
  6. washwas washed with 5% sodium bicarbonate and water
  7. extractionThe ether extract
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customto give an oil
  12. distillationThe oil was distilled 0.55-0.60 mm

Sources & evidence

ORD record
ord-29be0c8314ae4388b321930f0b5d101c
Source dataset
uspto-grants-1985_12
Patent number
US04560701

Reaction notes

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