Dimethylformamide → HCID 22000905, compound

HRID 1976291Notes

Reaction equation

HRID 1976291 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].Br[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C(OCC)(=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[O:10][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 127692,3,5-TrimethylphenolHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 22000905HCID 22000905, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,3,5-trimethylphenol (10.0 g), ethyl 4-bromobutyrate (12.6 ml), potassium carbonate (12.2 g), and dimethylformamide (DMF, 100 ml) was stirred at room temperature overnight. The reaction mixture was poured into a mixture of ethyl acetate (AcOEt) and water. The separated organic phase was washed with a saturated aqueous solution of sodium hydrocarbonate (sat. NaHCO3aq.), water, and brine, and was dried over magnesium sulfate (MgSO4). After evaporation, the resulting residue was purified by chromatography over silica gel (CHCl3 as eluent) to give ethyl 4-(2,3,5-trimethylphenoxy)butyrate (16.35 g) as an oil compound.

Workup

  1. washThe separated organic phase was washed with a saturated aqueous solution of sodium hydrocarbonate (sat. NaHCO3aq.), water, and brine
  2. dry with materialwas dried over magnesium sulfate (MgSO4)
  3. customAfter evaporation
  4. customthe resulting residue was purified by chromatography over silica gel (CHCl3 as eluent)

Sources & evidence

ORD record
ord-18d96b7fa67045ebb92afa90188225cd
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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