1-Hexanol → Hexyl (3-cyano-4,5-dimethoxyphenyl)glyoxylate

HRID 274505Notes

Reaction equation

HRID 274505 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[C:10]#[N:11])=[O:4].[Se](=O)=[O:18].[CH2:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(Cl)Cl>[C:10]([C:9]1[CH:12]=[C:5]([C:3](=[O:4])[C:2]([O:26][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:18])[CH:6]=[C:7]([O:15][CH3:16])[C:8]=1[O:13][CH3:14])#[N:11]

Participants

5

Reactant 3

HCID 81031-HexanolHCID 24007Selenium DioxideHCID 214589615-(Bromoacetyl)-2,3-dimethoxybenzonitrile

Product 1

HCID 17977685Hexyl (3-cyano-4,5-dimethoxyphenyl)glyoxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.45 g of 5-(bromoacetyl)-2,3-dimethoxybenzonitrile and 1.12 g of selenium dioxide are stirred at 120° for 18 hours in 10 ml of n-hexanol. After cooling to room temperature the mixture is diluted with 20 ml of methylene chloride and filtered. The filtrate is washed with water, dried over sodium sulfate and evaporated. The residue is chromatographed on 70 g of silica gel with hexane/ether (2:1). There is obtained hexyl (3-cyano-4,5-dimethoxy-phenyl)glyoxylate as an oil.

Workup

  1. filtrationfiltered
  2. washThe filtrate is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on 70 g of silica gel with hexane/ether (2:1)

Sources & evidence

ORD record
ord-19e6248e7a154a6fa89a8ff439cc9708
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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