Benzaldehyde → HCID 19026968, compound

HRID 1032956Notes

Reaction equation

HRID 1032956 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[N+:12]([O-])=O.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(=O)C.[Na+].[BH4-].[Na+].[OH-].[Na+]>C(O)(=O)C.C(O)C>[CH2:15]([NH:12][C:6]1[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:5]=1[O:4][CH2:3][O:2][CH3:1])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 14977438HCID 14977438, compound

Product 1

HCID 19026968HCID 19026968, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 2-methoxymethoxy-5-methylaniline (see Example 8) (15.6 g, 93.3 mmol), ethanol (100 ml), acetic acid (75 ml), benzaldehyde (19.0 ml, 187 mmol) and sodium acetate (15.5 g, 189 mmol) was added sodium borohydride (7.15 g, 189 mmol) under ice-cooling over a period of 30 minutes. The reaction mixture was stirred at 0° C. to room temperature for 1 hour. The reaction mixture was poured into 1N sodium hydroxide (500 ml) and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by column chromatography on silica gel to give white crystals. The crystals were recrystallized from chloroform/hexane to give the desired benzylaniline compound (1). Yield 25.2 g (86%, a mixture with dibenzyl compound in the ratio of 6:1).

Workup

  1. temperaturecooling over a period of 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe crude product was purified by column chromatography on silica gel
  7. customto give white crystals
  8. customThe crystals were recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-41140270e4874ca484b17cd34cf4b57f
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

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