2-Methoxyethanol → HCID 28603982, compound

HRID 2101094Notes

Reaction equation

HRID 2101094 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].[F:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1F)[CH:12]=[O:13].[NH4+].[Cl-]>CN(C=O)C>[F:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:7][CH2:6][CH2:5][O:4][CH3:3])[CH:12]=[O:13]

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 28603982HCID 28603982, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (7.3 g) was carefully added to a solution of 2-Methoxy-ethanol (15 ml) in DMF (200 ml) and the solution was stirred for 4 hours. 3,4-difluoro-benzaldehyde (14 g) was added to the mixture under N2 at 0° C., and the resulting mixture was slowly warmed to room temperature and stirred for another 6 hours. Saturated aqueous NH4Cl (200 ml) was added to the solution, and the mixture was extracted by ethyl acetate (500 ml×3). The organic layer was evaporated to give 3-Fluoro-4-(2-methoxy-ethoxy)-benzaldehyde as oil (15 g). LC-MS: m/e 199 (MH+).

Workup

  1. stirringstirred for another 6 hours
  2. extractionthe mixture was extracted by ethyl acetate (500 ml×3)
  3. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-66e871c7494f4ad7b907875beae51c34
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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