Allyl iodide → HCID 2192874, compound

HRID 1841764Notes

Reaction equation

HRID 1841764 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:4]([CH:5]=[O:6])[C:3]=1[OH:11].[CH2:12](I)[CH:13]=[CH2:14]>CN(C=O)C>[CH2:14]([O:11][C:3]1[C:2]([Cl:1])=[CH:9][C:8]([Cl:10])=[CH:7][C:4]=1[CH:5]=[O:6])[CH:13]=[CH2:12]

Participants

4

Reactant 2

HCID 11166Allyl iodideHCID 666603,5-Dichlorosalicylaldehyde

Product 1

HCID 2192874HCID 2192874, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 5.0 g of 3,5-dichlorosalicylaldehyde in 50 ml of DMF was treated with 3.23 g of potassium-tert.-butylate and 6.6 g of allyl iodide and stirred under argon at 65° C. After 2 hours the reaction mixture was concentrated, treated with ice-water and extracted with ethyl acetate. The organic phases were dried over sodium sulphate and concentrated. The residue was chrromatographed over silica gel and gave 5.5 g of 2-allyloxy-3,5-dichloro-benzaldehyde; MS (EI) m/z 230/232 M+.

Workup

  1. concentrationAfter 2 hours the reaction mixture was concentrated
  2. additiontreated with ice-water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phases were dried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-86a5feb1ff134ed49039a65070d69a9c
Source dataset
uspto-grants-2004_01
Patent number
US06683215B2

Reaction notes

Loading…