Water → HCID 86642400, compound

HRID 1951980Notes

Reaction equation

HRID 1951980 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([O:12][CH3:13])[CH:5]=1.[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19]Cl.O>O1CCCC1.CN(C)C=O>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([O:3][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 5195414-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 86642400HCID 86642400, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.8 g (41.2 mmol) of 60% sodium hydride is added in portions to a solution at 0° C. of 5.7 g (37.5 mmol) of 4-hydroxy-2-methoxy-benzaldehyde diluted in 30 ml of tetrahydrofuran and 30 ml of dimethylformamide. The reaction mixture is stirred at room temperature for 30 minutes and then 4.7 ml (41.2 mmol) of 2-methoxyethoxymethyl chloride is added dropwise. The reaction mixture is stirred at room temperature for 45 minutes 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 to give 8.6 g (95%) of 2-methoxy-4-(2-methoxy-ethoxymethoxy)-benzaldehyde in the form of a colorless oil.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 45 minutes
  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-248eef0e6b694cfcbdfaa5d5be644c32
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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