Methanol → HCID 53974214, compound

HRID 1684629Notes

Reaction equation

HRID 1684629 reaction equation
CO[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH:19]=1)[CH2:8][O:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.[CH3:20][O-:21].[Na+].[N+:23]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH:29]=O)([O-:25])=[O:24].C[OH:35]>>[CH2:8]([O:9][C:10]1[CH:11]=[CH:13][C:18]([O:21][CH3:20])=[CH:17][C:16]=1[C:15](=[O:35])[CH:14]=[CH:29][C:28]1[CH:31]=[CH:32][CH:33]=[C:26]([N+:23]([O-:25])=[O:24])[CH:27]=1)[C:7]1[CH:19]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 74493-NitrobenzaldehydeHCID 10942334Sodium MethoxideHCID 54312018HCID 54312018, compound

Product 1

HCID 53974214HCID 53974214, compoundYield 98%

Procedure

To a stirred solution of 13.5 g (0.053 mole) of 5-methoxy-2-benzyloxyacetophenone in 100 ml absolute methanol at ambient temperature was added 2.84 g (0.053 mole) sodium methoxide. After 20 minutes, 8.0 g (0.053 mole) 3-nitrobenzaldehyde was added and the reaction mixture was stirred at ambient temperature for 18 hours. The resulting precipitate was filtered, washed with absolute methanol and then dried in vacuo to afford 20.2 g (98%) the title product as a solid, mp 108°-110° C. Analysis calculated for C23H19NO3 : C, 70.94; H, 4.92; N, 3.60. Found: C, 71.07; H, 4.47; N, 3.46.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with absolute methanol
  3. customdried in vacuo

Sources & evidence

ORD record
ord-818f225ce85d413782ff3b742e04bb80
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

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