Potassium Carbonate → HCID 19698357, compound

HRID 1439898Notes

Reaction equation

HRID 1439898 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:17]([O:16][C:14]([CH2:13][O:11][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127886-Nitro-m-cresolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 19698357HCID 19698357, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-methyl-6-nitrophenol (30.62 g, 200 mmol) and tert-butyl bromacetate (46.8 g, 240 mmol) in acetonitrile (700 mL) in the presence of potassium carbonate (69.1 g, 500 mmol) was refluxed for 2 h. Inorganic materials were removed by filtration and the filtrate was concentrated. The residue was diluted with ethyl acetate, washed with brine, dried over magnesium sulfate, and extensively concentrated in vacuo to give 54.2 g of the title compound (quant): 1H NMR (CDCl3) δ7.82 (d, 1H, J=8.3 Hz), 6.87 (d, 1 H, J=8.3 Hz), 6.74 (s, 1H), 4.65 (s, 2H), 2.40 (s, 3H), 1.47 (s, 9H).

Workup

  1. temperaturewas refluxed for 2 h
  2. customInorganic materials were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationextensively concentrated in vacuo

Sources & evidence

ORD record
ord-59cf9eee027547db9cf59592b2a59a00
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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