Chloromethyl Methyl Ether → 5-Cyano-2-methoxymethoxycinnamaldehyde

HRID 1268212Notes

Reaction equation

HRID 1268212 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[CH:8]=[CH:9][CH:10]=[O:11])#[N:2].[CH3:14][O:15][CH2:16]Cl.C(N(CC)CC)C>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH2:14][O:15][CH3:16])=[C:7]([CH:12]=1)[CH:8]=[CH:9][CH:10]=[O:11])#[N:2]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 734500315-Cyano-2-hydroxycinnamaldehyde

Product 1

HCID 734499935-Cyano-2-methoxymethoxycinnamaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-cyano-2-hydroxycinnamaldehyde (2.3 g) in N,N-dimethylformamide (25 ml) were added methoxymethyl chloride (1.5 ml) and triethylamine (2.8 ml) in an ice bath and the mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with ethyl acetate. The extract was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo to give the desired compound (2.8 g, yield 98%) as a colorless solid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-30f5f04ccc6746888b47bc913101208f
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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