Tetrahydrofuran → HCID 21433608, compound

HRID 1576210Notes

Reaction equation

HRID 1576210 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1CCCC1.[C:12]([C:14]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1)#N.[OH-].[Na+]>O>[CH:12]([C:14]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1)=[O:7]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 912824-Oxo-1-phenylcyclohexanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 21433608HCID 21433608, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a well stirred suspension of 2.74 g. (0.072 mole) of lithium aluminum hydride in 170 ml. of tetrahydrofuran, a solution of 34.8 g. (0.143 mole) of 4-cyano-4-phenylcyclohexanone, ethylene ketal in 1700 ml. of tetrahydrofuran is added in a period of about 20 minutes. The mixture is stirred at room temperature for about 1.75 hours, then cooled in an icebath and treated successively with 2.8 ml. of water, 2.8 ml. of 15% sodium hydroxide solution and 8.2 ml. of water. The resulting inorganic gel is collected on a filter and rinsed with ether. The combined filtrates are then evaporated to dryness. A solution of the residue in 525 ml. of tetrahydrofuran and 52.5 ml. of 2.5 N hydrochloric acid is stirred at room temperature for about 15 minutes, treated with 17 g. of sodium bicarbonate solution and then evaporated to dryness. Ether is added to the residue and the organic layer evaporated to dryness to yield 34.07 g. (96.7% yield) of crude 4-formyl-4-phenylcyclohexanone, ethylene ketal, having a melting point of 51° to 66°C. Its infrared (IR) and NMR confirm its expected structure.

Workup

  1. additionsuspension of 2.74 g
  2. stirringThe mixture is stirred at room temperature for about 1.75 hours
  3. temperaturecooled in an icebath
  4. additiontreated successively with 2.8 ml
  5. customThe resulting inorganic gel is collected on
  6. filtrationa filter
  7. washrinsed with ether
  8. customThe combined filtrates are then evaporated to dryness
  9. stirringof 2.5 N hydrochloric acid is stirred at room temperature for about 15 minutes
  10. additiontreated with 17 g
  11. customof sodium bicarbonate solution and then evaporated to dryness
  12. additionEther is added to the residue
  13. customthe organic layer evaporated to dryness
  14. customto yield 34.07 g

Sources & evidence

ORD record
ord-87e963ebac6c4f819a7357be7c7c961c
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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