Acetic Anhydride → HCID 18690059, compound

HRID 2393429Notes

Reaction equation

HRID 2393429 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][Br:10])=[CH:6][CH:5]=1)([O-])=O.[C:13](OC(=O)C)(=[O:15])[CH3:14]>C(O)C.[Pt](=O)=O>[C:13]([NH:1][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][Br:10])=[CH:6][CH:5]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 792664-Nitrophenethyl bromide

Product 1

HCID 18690059HCID 18690059, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-nitrophenethyl bromide (23.8 g, 103.6 mmol) and acetic anhydride (9.8 ml, 103.6 mmol) in absolute ethanol (400 ml) was hydrogenated over platinum (IV) oxide (2.38 g) at 10 psi. The catalyst was removed by filtration and the solvent evaporated under vacuum. The remaining residue was purified by flash chromatography (silica gel, dichloromethane) to give 12.34 g of the title compound as a white solid. δ (250 MHz, CDCl3) 2.16 (3H, s), 3.12 (2H, t, J=7.5Hz), 3.53 (2H, t, J=7.5Hz), 7.15 (2H, d, J=8.4Hz), 7.45 (2H, d, J=8.4Hz).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated under vacuum
  3. customThe remaining residue was purified by flash chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-78152b14568245a3a3e946f5ae3eec5c
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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