Ethylene Glycol → HCID 21514762, compound

HRID 1576209Notes

Reaction equation

HRID 1576209 reaction equation
[C:1]([C:3]1([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#N.[OH-:20].[K+].C(O)C[OH:24]>O>[C:1]([C:3]1([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)([OH:24])=[O:20]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 12230240Cyclohexanecarbonitrile, 1-(1-naphthalenyl)-4-oxo-2×

Product 1

HCID 21514762HCID 21514762, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 11.21 g. (0.039 mole) of 4-cyano-4-(1-naphthyl)cyclohexanone, ethylene ketal (prepared in Example 23) and 12 g. of potassium hydroxide in 60 ml. of ethylene glycol is heated at reflux for about 16 hours. The resulting solution is allowed to cool, diluted with water and washed with ether. The aqueous layer is covered with ether and then cautiously acidified. The aqueous layer is extracted with two additional portions of ether and the extracts combined. The extracts are evaporated to dryness and the solid remaining is recrystallized from a mixture of ethyl acetate and cyclohexane to give 3.84 g. (31.5% yield) of 4-carboxy-4-(1-naphthyl)cyclohexanone, ethylene ketal, having a melting point of 174° to 177°C.

Workup

  1. additionA mixture of 11.21 g
  2. temperatureat reflux for about 16 hours
  3. temperatureto cool
  4. washwashed with ether
  5. extractionThe aqueous layer is extracted with two additional portions of ether
  6. customThe extracts are evaporated to dryness
  7. customthe solid remaining is recrystallized from a mixture of ethyl acetate and cyclohexane
  8. customto give 3.84 g

Sources & evidence

ORD record
ord-4340821396bb4565901180ed85dba8e4
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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