Potassium Carbonate → HCID 17985754, compound

HRID 751492Notes

Reaction equation

HRID 751492 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4]Br.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C)C=O.CCCCCC.C(OCC)C>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][O:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[CH3:8]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 935762-Methyl-5-nitrophenol

Product 1

HCID 17985754HCID 17985754, compoundYield 77.8%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

Add bromoacetaldehyde dimethylacetal (30.3 g, 179 mmol) to 2-methyl-5-nitrophenol (25 g, 163 mmol) and potassium carbonate (50 g, 362 mmol) in dimethylformamide (200 mL). Stir the mixture and reflux under nitrogen for 2.5 hours. Cool the mixture to 20° C. and add aqueous sodium hydroxide (200 mL, 1 M). Dilute the mixture with hexane and diethyl ether (1:1), then wash with 0.2M aqueous sodium hydroxide and aqueous saturated sodium chloride. Dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Precipitation of the product from hexane gives 30.6 g (77%) of the title compound, as a tan colored solid. 1H NMR (400 MHz, CDCl3) δ 7.78 (dd, 1 H, J=8.4, 2.4 Hz), 7.66 (d, 1 H, J=2.4 Hz), 7.26 (dd, 1 H, J=8.4, 0.8 Hz), 4.76 (t, 1 H, J=4.8 Hz), 4.09 (d, 2 H, J=35.2 Hz), 3.48 (s, 6 H), 2.32 (s, 3 H).

Workup

  1. temperaturereflux under nitrogen for 2.5 hours
  2. washwash with 0.2M aqueous sodium hydroxide and aqueous saturated sodium chloride
  3. dry with materialDry over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customPrecipitation of the product from hexane

Sources & evidence

ORD record
ord-4e45b2fabbc04fe98b6b6bd5566870a6
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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