Ethylene Glycol → HCID 12251395, compound

HRID 1580268Notes

Reaction equation

HRID 1580268 reaction equation
C1O[C:4]2([C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]32[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]3)OC1.O.NN.[OH-].[K+].[CH2:25](O)[CH2:26][OH:27]>>[CH2:25]1[O:18][C:15]2([CH2:14][CH2:13][C:5]3([CH2:4][C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH2:6]3)[CH2:17][CH2:16]2)[O:27][CH2:26]1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 131709907HCID 131709907, compound

Product 1

HCID 12251395HCID 12251395, compoundYield 85%

Procedure

A mixture of 5g. (0.0194 M) of spiro(cyclohexane 1,2'-indan)-1',4-dione 4-ethylene ketal [9](prepared as in Example 16B), 2.6ml. of hydrazine hydrate and 3.76 g. of potassium hydroxide in 50 ml. of ethylene glycol is heated at reflux for about 1.5 hours. Material is then removed by distillation to bring the pot temperature to 200° C. After about 5 hours of additional heating at reflux, the mixture is allowed to cool and diluted with water. The precipitated solid is collected on a filter, dried and recrystallized from petroleum ether to give 4 g. (85% yield) of spiro(cyclohexane-1,2'-indan)-4-one ethylene ketal [10], having a melting point of 70° to 74° C.

Workup

  1. temperatureat reflux for about 1.5 hours
  2. customMaterial is then removed by distillation
  3. customto 200° C
  4. temperatureAfter about 5 hours of additional heating
  5. temperatureat reflux
  6. temperatureto cool
  7. additiondiluted with water
  8. customThe precipitated solid is collected on a filter
  9. customdried
  10. customrecrystallized from petroleum ether
  11. customto give 4 g

Sources & evidence

ORD record
ord-69bc15abb34549fbb9465d1fc7066e11
Source dataset
uspto-grants-1976_01
Patent number
US03932425

Reaction notes

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