Ethylene Glycol → HCID 13121829, compound

HRID 904780Notes

Reaction equation

HRID 904780 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[O:19][CH:20]1[CH2:24][CH2:23][CH2:22][C:21]1=[O:25].[CH2:26](O)[CH2:27][OH:28].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[O:19][CH:20]1[CH2:24][CH2:23][CH2:22][C:21]21[O:28][CH2:27][CH2:26][O:25]2

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 13121828HCID 13121828, compound

Product 1

HCID 13121829HCID 13121829, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.2 g. of N-[4-bromo-3-(cyclopentanon-2-yloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 0.68 g. of ethyleneglycol, 0.2 g. of p-toluenesulfonic acid and 30 ml. of benzene was refluxed with stirring under removing water for 8 hours and the reaction mixture was cooled to room temperature and then, 20 ml. of ethyl acetate was added to the reaction mixture to extract the product. The extract was washed with water and dehydrated over sodium sulfate and the solvent was distilled off and the product was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 1:4) to obtain 1.35 g. of Compound No. 9 shown in Table 1.

Workup

  1. additionA mixture of 2.2 g
  2. extractionto extract the product
  3. washThe extract was washed with water
  4. distillationthe solvent was distilled off
  5. customthe product was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 1:4)
  6. customto obtain 1.35 g

Sources & evidence

ORD record
ord-4c667b5bd75b4815871ce45aacfb875a
Source dataset
uspto-grants-1983_12
Patent number
US04420327

Reaction notes

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