Ethylene Glycol → 1-(3,4-Dimethoxyphenyl)-5,5-ethylenedioxy-7-(4-methoxyphenyl)-2-nitroheptane

HRID 1589363Notes

Reaction equation

HRID 1589363 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([N+:27]([O-:29])=[O:28])[CH2:13][CH2:14][C:15](=[O:26])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[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.[CH2:41](O)[CH2:42][OH:43].C1C=CC=CC=1>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([N+:27]([O-:29])=[O:28])[CH2:13][CH2:14][C:15]2([O:43][CH2:42][CH2:41][O:26]2)[CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 130650201-(3,4-Dimethoxyphenyl)-7-(4-methoxyphenyl)-2-nitro-5-heptanone

Product 1

HCID 130650211-(3,4-Dimethoxyphenyl)-5,5-ethylenedioxy-7-(4-methoxyphenyl)-2-nitroheptane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 1 l. r.b. flask equipped with a Dean-Stark trap was placed 22 g. (0.055 mole) of 1-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)-2-nitro-5-heptanone, 2 g. of p-toluenesulfonic acid, 25 ml. of ethylene glycol, and 500 ml. of benzene, the mixture was refluxed until no more water was separated, and then cooled to room temperature. The dark solution was poured into cold dil. NaHCO3 solution and extracted with ethyl acetate. The organic layer was backwashed with water and dried over anhydrous MgSO4. Upon removing solvent by distillation a gray solid was obtained from trituration with ether. Recrystallization from 80% ethanol yielded 25 g. of product as a white solid; m.p. 98°-100° C.

Workup

  1. customflask equipped with a Dean-Stark trap
  2. customwas separated
  3. additionThe dark solution was poured into cold dil. NaHCO3 solution
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous MgSO4
  6. customUpon removing solvent
  7. distillationby distillation a gray solid
  8. customwas obtained from trituration with ether
  9. customRecrystallization from 80% ethanol
  10. customyielded 25 g

Sources & evidence

ORD record
ord-52f1d837af2c4f00a071ecc5f5234ccd
Source dataset
uspto-grants-1986_02
Patent number
US04569941

Reaction notes

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