Ethylene Glycol → HCID 20453280, compound

HRID 1462503Notes

Reaction equation

HRID 1462503 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([C:15]#N)([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)[CH2:6][CH2:5]2)[O:3]C1.[OH-:18].[Na+].C(O)C[OH:22].CCOCC>O>[C:15]([C:7]1([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]1)([OH:22])=[O:18]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 12595544HCID 12595544, compound

Product 1

HCID 20453280HCID 20453280, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.98 g. (0.02 mole) of 4-cyano-4-(2-thienyl)cyclohexanone ethylene ketal and 0.70 g. (0.02 mole) of sodium hydroxide in 40 ml. ethylene glycol is heated overnight at reflux. The mixture is allowed to cool and diluted with water. The solution is then cooled in ice, covered with ether and cautiously acidified. The organic layer is separated and the aqueous layer is washed twice more with ether. The extracts are combined, washed once with brine and taken to dryness. The residual solid is recrystallized from methylene chloride:Skellysolve B to afford 4.64 g. (72% yield) of 4-carboxy-4-(2-thienyl)cyclohexanone, ethylene ketal, m.p. 125°-127° C.

Workup

  1. additionA mixture of 4.98 g
  2. temperatureat reflux
  3. temperatureto cool
  4. temperatureThe solution is then cooled in ice
  5. customThe organic layer is separated
  6. washthe aqueous layer is washed twice more with ether
  7. washwashed once with brine
  8. customThe residual solid is recrystallized from methylene chloride
  9. customSkellysolve B to afford 4.64 g

Sources & evidence

ORD record
ord-884ed62a1617430e9a3c21b065a1aba4
Source dataset
uspto-grants-1984_07
Patent number
US04460604

Reaction notes

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