Iodine → ethyl 6-oxodecanoate

HRID 851836Notes

Reaction equation

HRID 851836 reaction equation
[CH2:1](I)[CH2:2][CH2:3][CH3:4].II.[Cl-].[CH2:9]([O:11][C:12](=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)[CH3:10].S(=O)(=O)(O)O>[Cu].[Zn].O.C1(C)C=CC=CC=1.C(OCCCC)(=O)C>[O:19]=[C:17]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:16][CH2:15][CH2:14][CH2:13][C:12]([O:11][CH2:9][CH3:10])=[O:20]

Participants

9

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 10962Butyl iodideHCID 86624202Adipic acid monoethyl ester chloride

Product 1

HCID 11063798ethyl 6-oxodecanoate

Reagents, catalysts & solvents 4

HCID 10290809Zinc copper coupleCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 31272Butyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of activated zinc-copper catalyst (11.5 g), butyl acetate (4 g), toluene (5 g), butyl iodide (15 g) and iodine (3 mg) was heated at 110-120° C. for 2 hours. The mixture was then added dropwise with adipic acid monoethyl ester chloride(15.7 g) at 0° C., and then was allowed to react. After the reaction was completed, ice-cooled water was added to the reaction solution, and then decomposed with dilute sulfuric acid. The oily layer was extracted with ether, washed with aqueous sodium hydrogencarbonate, washed with water, and then dried. The residue was evaporated to remove the solvent, and then distilled, thereby giving ethyl 6-oxodecanoate (8.1 g).

Workup

  1. customto react
  2. additionwas added to the reaction solution
  3. extractionThe oily layer was extracted with ether
  4. washwashed with aqueous sodium hydrogencarbonate
  5. washwashed with water
  6. customdried
  7. customThe residue was evaporated
  8. customto remove the solvent
  9. distillationdistilled

Sources & evidence

ORD record
ord-f8e59d31c55344dab18d4c459cf6a61a
Source dataset
uspto-grants-2007_08
Patent number
US07252849B2

Reaction notes

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