Water → HCID 68602836, compound

HRID 1951978Notes

Reaction equation

HRID 1951978 reaction equation
[H-].[Na+].[C:3]([O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([O:16][CH3:17])[CH:10]=1)(=[O:5])[CH3:4].Cl[CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24].O>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[C:3]([O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])=[C:11]([O:16][CH3:17])[CH:10]=1)(=[O:5])[CH3:4]

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 58508461HCID 58508461, compound

Product 1

HCID 68602836HCID 68602836, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.9 g (23 mmol) of 60% sodium hydride is added in portions to a previously cooled solution of 4 g (19 mmol) of (4-hydroxy-3-methoxy-phenyl)-ethyl acetate in 20 ml of tetrahydrofuran and 20 ml of dimethylformamide. After stirring at room temperature for 45 minutes, 2.4 ml (21 mmol) of 1-chloromethoxy-2-methoxy-ethane is added dropwise. After stirring at room temperature for 1 hour, water and ethyl acetate are added. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. 5.5 g (97%) of [3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-ethyl acetate is obtained.

Workup

  1. stirringAfter stirring at room temperature for 1 hour
  2. washThe organic phase is washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9dd3ad35f3df44b5886b506a36b9d663
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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