Sodium hydride → HCID 68600595, compound

HRID 1951968Notes

Reaction equation

HRID 1951968 reaction equation
[H-].[Na+].[C:3]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)(=[O:5])[CH3:4].Cl[CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21]>O1CCCC1.CN(C)C=O>[C:3]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:12][CH:13]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 11788491HCID 11788491, compound

Product 1

HCID 68600595HCID 68600595, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.53 g (132 mmol) of 60% sodium hydride is added in portions to a solution at 0° C. of 20 g (120 mmol) of (4-hydroxy-phenyl)-methyl acetate diluted in 100 ml of tetrahydrofuran and 100 ml of dimethylformamide. The reaction mixture is stirred at room temperature, and then 15 ml (132 mmol) of 1-chloromethoxy-2-methoxy-ethane is added dropwise. After stirring at room temperature for 2 hours, then adding water, the reaction mixture is extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and then dried over magnesium sulfate. After evaporation of the solvents, 25 g (86%) of [4-(2-methoxy-ethoxymethoxy)-phenyl]-methyl acetate is obtained in the form of a colorless oil.

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. extractionadding water, the reaction mixture is extracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvents

Sources & evidence

ORD record
ord-46fcd686c9dc4ae89aba2ac81403bb3a
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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