Water → HCID 68527017, compound

HRID 884079Notes

Reaction equation

HRID 884079 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[CH:9]=[C:10]([CH3:15])[C:11]([OH:14])=[CH:12][CH:13]=1.Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].O>CN(C=O)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH3:15])[CH:9]=1)[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 760815-Amino-2-hydroxytoluene

Product 1

HCID 68527017HCID 68527017, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (5.04 g, 36.5 mmol) was added at room temperature to a solution of 4-amino-o-cresol (3.00 g, 24.4 mmol) and ethyl bromoacetate (2.70 mL, 24.4 mmol) in DMF (30 mL). The resulting solution was stirred at room temperature for 1.5 hours. Water was added to the reaction mixture, and extracted with ethyl acetate. The ethyl acetate layer was washed with brine. The ethyl acetate layer was dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), to thereby yield 5.10 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-e9e25c14067a4b749513586c2ed19cdd
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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