Dimethylformamide → HCID 17861278, compound

HRID 1294100Notes

Reaction equation

HRID 1294100 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH3:14].Br[CH2:16][C:17]([O:19][CH3:20])=[O:18].CN(C)C=O.[H-].[Na+]>O>[CH3:11][O:10][CH2:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:12][CH2:13][CH3:14])=[C:2]([CH:7]=1)[O:1][CH2:16][C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 17861346HCID 17861346, compound

Product 1

HCID 17861278HCID 17861278, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-hydroxy-4-methoxymethoxy-1-propylbenzene (1.50 g), methyl bromoacetate (1.39 g) and N,N-dimethylformamide (20 mL) was added sodium hydride (60%, oil, 1.50 g) under ice-cooling. The reaction mixture was stirred at room temperature for 13 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give methyl 2-(5-methoxymethoxy-2-propylphenoxy)acetate as a colorless oil (1.60 g, 78%) from a fraction eluted with ethyl acetate-hexane (1:6, v/v).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1aab9ecd3c8440bd9e647cbc824efb24
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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