Cyclohexane ethylacetate → HCID 58136303, compound

HRID 877214Notes

Reaction equation

HRID 877214 reaction equation
[CH3:1][C:2]([CH3:17])([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].C1CCCCC1.C(OCC)(=O)C>[Pd].C(O)C>[NH2:14][C:10]1[CH:9]=[C:8]([CH2:7][C:2]([CH3:17])([CH3:1])[C:3]([O:5][CH3:6])=[O:4])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 21867204Cyclohexane ethylacetateHCID 58136634HCID 58136634, compound

Product 1

HCID 58136303HCID 58136303, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

At room temperature, 1 g of palladium on carbon (10%) was added to a solution of 12 g (51.42 mmol) of methyl 2,2-dimethyl-3-(3-nitrophenyl)propanoate in 200 ml of ethanol, and the mixture was hydrogenated under atmospheric pressure for 12 hours. After the reaction had gone to completion (monitored by TLC; mobile phase cyclohexane/ethyl acetate 1:1), the reaction solution was filtered through kieselguhr and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→1:1). This gave 9.2 g (44.39 mmol, 86% of theory) of the title compound.

Workup

  1. filtrationthe reaction solution was filtered through kieselguhr
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→1:1)

Sources & evidence

ORD record
ord-3d6d2558f27c479e9f00961e7ba68be3
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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