Water → HCID 68601983, compound

HRID 1951985Notes

Reaction equation

HRID 1951985 reaction equation
[H-].[Na+].[C:3]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([Cl:15])[CH:9]=1)(=[O:5])[CH3:4].[CH3:16][O:17][CH2:18][CH2:19][O:20][CH2:21]Cl.O>O1CCCC1.CN(C)C=O>[C:3]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:10]([Cl:15])[CH:9]=1)(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 14119312HCID 14119312, compound

Product 1

HCID 68601983HCID 68601983, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.75 g (68.4 mmol) of 60% sodium hydride is added in portions to a solution at 0° C. of 11 g (57 mmol) of (3-chloro-4-hydroxy-phenyl)-methyl acetate diluted in 60 ml of tetrahydrofuran and 60 ml of dimethylformamide. The reaction mixture is stirred at room temperature for 45 minutes and then 7.2 ml (62.7 mmol) of 2-methoxyethoxymethyl chloride is added dropwise. The reaction mixture is stirred at room temperature for 2 hours and then the reaction mixture is treated by adding water and extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. The raw product is purified by silica column chromatography, eluted with a heptane/ethyl acetate mixture 70/30. 10.6 g (66%) of [3-chloro-4-(2-methoxy-ethoxymethoxy)-phenyl]-methyl acetate is obtained in the form of a colorless oil.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 2 hours
  2. additionthe reaction mixture is treated
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe raw product is purified by silica column chromatography
  9. washeluted with a heptane/ethyl acetate mixture 70/30

Sources & evidence

ORD record
ord-21efd12bc1254643a9a35b9194b1db21
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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