Potassium Carbonate → HCID 17985754, compound

HRID 910097Notes

Reaction equation

HRID 910097 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, compound

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 and reflux under nitrogen for 2.5 hours. Cool to 20° C. temperature and add aqueous sodium hydroxide (200 mL, 1 M). Dilute the mixture with hexane, diethyl ether (1:1), wash with 0.2 M aqueous sodium hydroxide, aqueous saturated sodium chloride, dry the organic phase over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Recrystallize the product from hexane to obtain the desired compound, as tan colored solid 30.6 gm (77%).

Workup

  1. temperaturereflux under nitrogen for 2.5 hours
  2. washwash with 0.2 M aqueous sodium hydroxide, aqueous saturated sodium chloride
  3. dry with materialdry the organic phase over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customRecrystallize the product from hexane

Sources & evidence

ORD record
ord-c723dfc10cee47bca2b3d78ecc39ed15
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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