Water → 1-Ethylenedioxy-2-(6-carboxyhexyl)-3-nitromethyl-cyclopentane

HRID 27283Notes

Reaction equation

HRID 27283 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH:14]([CH2:15][N+:16]([O-:18])=[O:17])[CH2:13][CH2:12][C:11]1=[O:19])([OH:3])=[O:2].[C:20]1([CH3:30])C=CC(S(O)(=O)=O)=CC=1.[OH2:31]>C1C=CC=CC=1.C(O)CO>[CH2:30]1[CH2:20][O:31][C:10]2([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:1]([OH:3])=[O:2])[CH:14]([CH2:15][N+:16]([O-:18])=[O:17])[CH2:13][CH2:12][CH:11]2[O:19]1

Participants

6

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 233445592-(6-Carboxyhexyl)-3-nitromethyl-cyclopentan-1-one

Product 1

HCID 705892141-Ethylenedioxy-2-(6-carboxyhexyl)-3-nitromethyl-cyclopentane

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 241BenzeneSolvent

Procedure

The solution of 2-(6-carboxyhexyl)-3-nitromethyl-cyclopentan-1-one, methyl ester (14 g.) in benzene (200 ml.), ethylene glycol (16.1 ml.), p-toluenesulphonic acid (0.315 g.), is heated to boiling for 16 hours. The reaction water is separated in a Marcusson apparatus. The mixture is washed with an aqueous saturated NaHCO3 -solution (50 ml.), then with water to neutrality, dried over sodium sulphate and the solvent is evaporated in vacuo. From the oily residue, by chromatography on silica (300 g.) and elution with benzene/ethyl acetate (6:1), 13 g. of 1-ethylenedioxy-2-(6-carboxyhexyl)-3-nitromethyl-cyclopentane, methyl ester, are obtained.

Workup

  1. customis separated in a Marcusson apparatus
  2. washThe mixture is washed with an aqueous saturated NaHCO3 -solution (50 ml.)
  3. dry with materialwith water to neutrality, dried over sodium sulphate
  4. customthe solvent is evaporated in vacuo
  5. washFrom the oily residue, by chromatography on silica (300 g.) and elution with benzene/ethyl acetate (6:1), 13 g

Sources & evidence

ORD record
ord-844ea57a042f4a99b757d9b37d4ac6c2
Source dataset
uspto-grants-1980_09
Patent number
US04220798

Reaction notes

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