2-[1-(2,4-Dimethoxyphenyl)hexyl]malonic acid → 3-(2,4-Dimethoxyphenyl)octanoic acid

HRID 1637485Notes

Reaction equation

HRID 1637485 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([CH:17](C(O)=O)[C:18]([OH:20])=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:17][C:18]([OH:20])=[O:19]

Participants

3

Reactant 1

HCID 193484652-[1-(2,4-Dimethoxyphenyl)hexyl]malonic acid

Product 1

HCID 193486193-(2,4-Dimethoxyphenyl)octanoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 6.57 g of 2-[1-(2,4-dimethoxyphenyl)hexyl]malonic acid [prepared as described in step (i) above] in 60 ml of xylene was heated under reflux for 3 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 100 g of silica gel, using a gradient elution method, with mixtures of methylene chloride and methanol ranging from 1:0 to 10:1 by volume as the eluent, to give 4.55 g (a total yield of 74% over the two steps) of the title compound as crystals, melting at 52-53° C. (from hexane).

Workup

  1. temperatureunder reflux for 3 hours
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. customthe resulting residue was purified by column chromatography through 100 g of silica gel
  4. washa gradient elution method

Sources & evidence

ORD record
ord-321ef7d95d4d47b8b5cdf26191d6b7aa
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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