Salicylaldehyde → 2-(Methoxymethoxy)benzaldehyde

HRID 708303Notes

Reaction equation

HRID 708303 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[H-].[Na+].Cl[CH2:13][O:14][CH3:15]>CN(C)C=O>[CH3:13][O:14][CH2:15][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 108774852-(Methoxymethoxy)benzaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Salicylaldehyde (3 g) was slowly added to a N,N-dimethylformamide solution (50 mL) of sodium hydride (55%, 1.2 g) at 0° C. The mixture was stirred at the same temperature for 1 hour. Subsequently, chloromethylmethyl ether (2.9 g) was added thereto. After confirmation of the degree of reaction progress by TLC, the reaction was quenched with an aqueous solution of ammonium chloride. The organic layer was extracted with ethyl acetate and then was dried over anhydrous magnesium sulfate. The crude product obtained by concentrating the organic phase was purified by column chromatography to obtain 3.9 g (yield: 96%) of 2-methoxymethoxybenzaldehyde.

Workup

  1. customAfter confirmation of the degree of reaction progress by TLC
  2. customthe reaction was quenched with an aqueous solution of ammonium chloride
  3. extractionThe organic layer was extracted with ethyl acetate
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customThe crude product obtained
  6. concentrationby concentrating the organic phase
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1429deee810644a894868ee1518d1230
Source dataset
uspto-grants-2015_11
Patent number
US09176257B2

Reaction notes

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