Ethylene Glycol → HCID 86732931, compound

HRID 1580265Notes

Reaction equation

HRID 1580265 reaction equation
CO[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]([OH:22])[CH2:20]O.[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:20]1[O:12][C:8]2([C:9]3[C:5](=[CH:4][C:3]([CH3:23])=[CH:11][CH:10]=3)[CH2:6][C:7]32[CH2:13][CH2:14][C:15](=[O:18])[CH2:16][CH2:17]3)[O:22][CH2:19]1

Participants

5

Reactant 3

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

Product 1

HCID 86732931HCID 86732931, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.06 g. (0.00905 M) of 5'-methylspiro(cyclohexane-1,2'-indan)-1',4-dione [8 ] (prepared in Example 13B), 0.56 g. (0.50 ml.) of ethylene glycol and 0.1 g. of p-toluenesulfonic acid in 50 ml. of benzene is heated at reflux under a Dean-Stark trap for about 2 hours. The mixture is allowed to cool, washed with aqueous sodium bicarbonate solution then water and evaporated to dryness. The residual solid is recrystallized from methylene chloride: cyclohexane to give 1.96 g. (86%) of 5'-methyl-spiro(cyclohexane-1,2'-indan)-1',4-dione 4-ethylene ketal-[9], melting at 124° to 127° C.

Workup

  1. additionA mixture of 2.06 g
  2. temperatureat reflux under a Dean-Stark trap for about 2 hours
  3. temperatureto cool
  4. washwashed with aqueous sodium bicarbonate solution
  5. customwater and evaporated to dryness
  6. customThe residual solid is recrystallized from methylene chloride
  7. customcyclohexane to give 1.96 g

Sources & evidence

ORD record
ord-3adaf1274ee24959babe93804ddab002
Source dataset
uspto-grants-1976_01
Patent number
US03932425

Reaction notes

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