Ethylene Glycol → 1-(3',4'-Dimethoxyphenyl)-7-(4'-fluorophenyl)-2-nitro-5-heptanone ethylene ketal

HRID 66470Notes

Reaction equation

HRID 66470 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([N+:26]([O-:28])=[O:27])[CH2:13][CH2:14][C:15](=[O:25])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:40](O)[CH2:41][OH:42]>C1CCCCC1>[CH2:41]1[O:42][C:15]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([CH2:14][CH2:13][CH:12]([N+:26]([O-:28])=[O:27])[CH2:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[O:25][CH2:40]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 201642101-(3',4'-Dimethoxyphenyl)-7-(4'-fluorophenyl)-2-nitro-5-heptanone

Product 1

HCID 566265521-(3',4'-Dimethoxyphenyl)-7-(4'-fluorophenyl)-2-nitro-5-heptanone ethylene ketal

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Into a 1 l. r.b. flask equipped with a Dean-Stark trap was placed 79 g (0.2 mole) of 1-(3',4'-dimethoxyphenyl)-7-(4'-fluorophenyl)-2-nitro-5-heptanone, 38 g p-toluenesulfonic acid, 120 ml ethylene glycol and 400 ml cyclohexane. The mixture was allowed to reflux overnight, then concentrated in vacuo. Dil NaHCO3 solution was added to the residue and extracted with methylene chloride. The organic layer was backwashed with water, dried over anh MgSO4, filtered and concentrated under reduced pressure to obtain 84.8 g of oily product.

Workup

  1. customflask equipped with a Dean-Stark trap
  2. temperatureto reflux overnight
  3. concentrationconcentrated in vacuo
  4. additionDil NaHCO3 solution was added to the residue
  5. extractionextracted with methylene chloride
  6. dry with materialdried over anh MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bae0000642044e9ba37819f228b9598f
Source dataset
uspto-grants-1982_08
Patent number
US04342692

Reaction notes

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