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

HRID 2254777Notes

Reaction equation

HRID 2254777 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([O:16][CH2:17]C)[C:8]([O:13][CH2:14]C)=[C:9]([CH:12]=1)[C:10]#[N:11])=[O:4].[Se](=O)=[O:20].[CH2:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[C:10]([C:9]1[CH:12]=[C:5]([C:3](=[O:4])[C:2]([O:28][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:20])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[O:13][CH3:14])#[N:11]

Participants

5

Reactant 3

HCID 81031-HexanolHCID 24007Selenium DioxideHCID 197430625-(Bromoacetyl)-2,3-diethoxybenzonitrile

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-diethoxybenzonitrile 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-dimethoxyphenyl)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-0672cd82b4d94bdd8b1d71877e7777eb
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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