Ethylene Glycol → HCID 86732932, compound

HRID 1580266Notes

Reaction equation

HRID 1580266 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[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][OH:21].[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:19]1[O:22][C:6]2([C:5]3[C:9](=[CH:10][CH:23]=[C:3]([CH3:11])[CH:4]=3)[CH2:8][C:7]32[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]3)[O:21][CH2:20]1

Participants

5

Reactant 3

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

Product 1

HCID 86732932HCID 86732932, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 7.3 g. (0.032 M) of 6'-methylspiro(cyclohexane-1,2'-indan)-1',4-dione [8] (prepared in Example 14B), 2.15 g. (1.95 ml.) of ethylene glycol and 0.5 g. of p-toluenesulfonic acid in 200 ml. of benzene is heated at reflux under a Dean-Stark trap for about 5 hours. The mixture is allowed to cool, washed successively with aqueous sodium bicarbonate solution, water and brine and evaporated to dryness. The residual solid is recrystallized from methylene chloride: Skellysolve B to give 7.94 g. (91% yield) of 6'-methylspiro(cyclohexane-1,2'-indan)-1',4-dione 4-ethylene ketal [9] melting at 116° to 118° C.

Workup

  1. additionA mixture of 7.3 g
  2. temperatureat reflux under a Dean-Stark trap for about 5 hours
  3. temperatureto cool
  4. washwashed successively with aqueous sodium bicarbonate solution, water and brine
  5. customevaporated to dryness
  6. customThe residual solid is recrystallized from methylene chloride
  7. customSkellysolve B to give 7.94 g

Sources & evidence

ORD record
ord-92184029c49b41ad88ac4641f2a484b3
Source dataset
uspto-grants-1976_01
Patent number
US03932425

Reaction notes

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