Ethylene Glycol → HCID 86732933, compound

HRID 1580267Notes

Reaction equation

HRID 1580267 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]1([CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1)[CH2:6]2.[CH2:19](O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:20]1[O:21][C:8]2([C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH2:6][C:7]32[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]3)[O:12][CH2:19]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 2755446HCID 2755446, compound

Product 1

HCID 86732933HCID 86732933, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4.89 g. (0.0196 M) of 6'-methoxyspiro(cyclohexane-1,2'-indan)-1',4-dione [8] (prepared as in Example 15B), 1.21 g. of ethylene glycol and 0.2 g. of p-toluenesulfonic acid in 100 ml. of benzene is heated at reflux under a Dean-Stark trap for about 5 hours. The mixture is allowed to cool, washed with aqueous sodium bicarbonate solution and evaporated to dryness. The residue is recrystallized twice from methylene chloride: Skellysolve B to give 4.13 g. (73% yield) of 5'-methoxyspiro(cyclohexane-1,2'-indan)-1',4-dione 4-ethylene ketal [9 ] having a melting point of 142° to 144° C.

Workup

  1. additionA mixture of 4.89 g
  2. temperatureat reflux under a Dean-Stark trap for about 5 hours
  3. temperatureto cool
  4. washwashed with aqueous sodium bicarbonate solution
  5. customevaporated to dryness
  6. customThe residue is recrystallized twice from methylene chloride
  7. customSkellysolve B to give 4.13 g

Sources & evidence

ORD record
ord-bafa132d49a44653a8daa1eb7da9adf0
Source dataset
uspto-grants-1976_01
Patent number
US03932425

Reaction notes

Loading…