Water → HCID 18357788, compound

HRID 617382Notes

Reaction equation

HRID 617382 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:5]=1[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([OH:19])[C:15]([O:17][CH3:18])=[O:16].[CH3:25]I.O>CN(C)C=O>[CH3:3][C:4]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:5]=1[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([O:19][CH3:25])[C:15]([O:17][CH3:18])=[O:16].[CH3:3][C:4]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:5]=1[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([OH:19])[C:15]([O:17][CH3:18])=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18357788HCID 18357788, compound

Product 2

HCID 11781996HCID 11781996, compoundHCID 18357788HCID 18357788, compoundYield 191.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% oily sodium hydride (0.13 g, 3.3 mmol) was added to a solution of methyl 2-[2-(2,5-dimethylphenoxymethyl)-phenyl]-2hydroxyacetate (0.72 g, 2.4 mmol) and methyl iodide (0.68 g, 4.8 mmol) in N,N-dimethylformamide (6 ml) at 0° C. with stirring. After 30 minutes, ice and water were added in this order, and the mixture was extracted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=9/1) to give the desired compound methyl 2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-hydroxyacetate (0.69 g, 92%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-3e40d12bef9941289764503238f1a996
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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