Ethylene Glycol → 3-(2,4-Dimethoxyphenyl)octanoic acid

HRID 1637555Notes

Reaction equation

HRID 1637555 reaction equation
[OH-:1].[K+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])CC#N.Cl.CCCCC.[CH2:28]([OH:31])[CH2:29]O>>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:29][C:28]([OH:31])=[O:1]

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 8003PentaneHCID 14797Potassium HydroxideHCID 19348443(-)-2-(2,4-Dimethoxyphenyl)heptyl cyanide

Product 1

HCID 193486193-(2,4-Dimethoxyphenyl)octanoic acidYield 87%

Procedure

1.00 g (17.8 mmol) of potassium hydroxide was added to a solution of 1.27 g (4.86 mmol) of (-)-2-(2,4-dimethoxyphenyl)heptyl cyanide [prepared as described in step (ii) above] in 6 ml of ethylene glycol, and the resulting mixture was heated under reflux for 2.5 hours in an atmosphere of nitrogen. At the end of this time, the reaction mixture was cooled to room temperature, after which it was acidified with 1 N aqueous hydrochloric acid and then extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 100 g of silica gel, using a 1:2 by volume mixture of ethyl acetate and hexane as the eluent, to give 1.19 g (yield 87%) of the title compound as crystals, melting at 51-52° C. (from pentane).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2.5 hours in an atmosphere of nitrogen
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter which the solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through 100 g of silica gel
  8. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-73a4d36e8a90451f9ffa8102d8cd1765
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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