Dimethylformamide → Benzyloxyacetaldehyde diethyl acetal

HRID 1805939Notes

Reaction equation

HRID 1805939 reaction equation
[C:1]([O-:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15]Br)[CH3:12].CN(C)C=O>O>[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15][O:9][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 517055Sodium Benzoate

Product 1

HCID 4321487Benzyloxyacetaldehyde diethyl acetalYield 94.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 2-L, three-necked, round-bottomed flask fitted with a mechanical stirrer, a reflux condenser and a glass stopper is added sodium benzoate (0.579 mol, 83.44 g, 1.1 equiv.), bromoacetaldehyde diethyl acetal (0.526 mol, 103.74 g, 1.0 equiv.) and N,N-dimethylformamide (1.0 L). The reaction was heated to reflux and stirred while monitoring progress by thin layer chromatography (TLC). When determined to be complete, the reaction was allowed to cool to ambient temperature and diluted with water (2.0 L). The product was extracted with methyl tert-butyl ether. The organic phase was dried over magnesium sulfate and concentrated by rotary evaporation to give 2-(benzyloxy)acetaldehyde diethyl acetal (111.85 g, 81.1% yield). The crude product was advanced to the next reaction step without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. extractionThe product was extracted with methyl tert-butyl ether
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-1054e802d7b7452193664c41836637fb
Source dataset
uspto-grants-2013_01
Patent number
US08354546B2

Reaction notes

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