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

HRID 1589375Notes

Reaction equation

HRID 1589375 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]([Cl: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]([Cl: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 201641881-(3',4'-Dimethoxyphenyl)-7-(4'-chlorophenyl)-2-nitro-5-heptanone

Product 1

HCID 566381321-(3',4'-Dimethoxyphenyl)-7-(4'-chlorophenyl)-2-nitro-5-heptanone ethylene ketal

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Into 1 l. r.b. flask equipped with a Dean Stark trap was placed 65 g (0.16 mole) of 1-(3',4'-dimethoxyphenyl)-7-(4'-chlorophenyl)-2-nitro-5-heptanone, 2 g p-toluenesulfonic acid, 100 ml ethylene glycol and 400 ml of 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 45.3 g of an oil which solidified on drying at room temperature under vacuum.

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-237573b929ee42749fcaa3fd7f4c98b4
Source dataset
uspto-grants-1986_02
Patent number
US04569941

Reaction notes

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