Acetophenone → HCID 14496781, compound

HRID 1464152Notes

Reaction equation

HRID 1464152 reaction equation
[H-].[Na+].CCCCC.[C:8]([O:17]C)(=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14].[C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])[CH3:20]>CO.O1CCCC1>[C:22]1([C:19](=[O:21])[CH2:20][C:8](=[O:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH3:14])[CH3:15])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 7410Acetophenone2×HCID 8003PentaneHCID 24758Sodium hydrideHCID 520188Isooctanoic acid, methyl ester

Product 1

HCID 14496781HCID 14496781, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A dispersion of 16.9 G (0.4 mole) of 56% by weight sodium hydride in mineral oil is slurried with n-pentane under nitrogen, the supernatant liquid is removed by suction with a sintered glass tip tube. This process is repeated three times before 500 ml of dry tetrahydrofuran and 75.8 G (0.48 mole) of methyl isooctanoate are added. The resultant mixture is heated to reflux temperature with agitation. A total of 48 G (0.4 mole) of acetophenone is added to the above refluxing mixture over a 3 hour period of time. The system is maintained at reflux temperature for an additional one half hour after the acetophenone addition is completed. Approximately 20 ml of methanol is added to the above mixture at room temperature to destroy any unreacted sodium hydride. The reaction mixture is then poured into a vigorously stirred mixture of 75 ml of concentrated hydrochloric acid and 250 G of ice. When most of the ice has melted the solution is extracted twice with 242 ml of heptane per extraction. The combined heptane extracts are successively washed with water, 10% sodium carbonate solution and again with water. The heptane solution is dried with sodium sulfate, filtered, the volatiles removed at reduced pressure and the residue distilled to yield 1-phenylisodecane-1,3-dione.

Workup

  1. customthe supernatant liquid is removed by suction with a sintered glass tip tube
  2. additionare added
  3. temperatureto reflux temperature with agitation
  4. temperatureThe system is maintained
  5. temperatureat reflux temperature for an additional one half hour
  6. customto destroy any unreacted sodium hydride
  7. additionThe reaction mixture is then poured into a vigorously stirred mixture of 75 ml of concentrated hydrochloric acid and 250 G of ice
  8. extractionis extracted twice with 242 ml of heptane per extraction
  9. washThe combined heptane extracts are successively washed with water, 10% sodium carbonate solution and again with water
  10. dry with materialThe heptane solution is dried with sodium sulfate
  11. filtrationfiltered
  12. customthe volatiles removed at reduced pressure
  13. distillationthe residue distilled

Sources & evidence

ORD record
ord-ecfdc9754ace4e60a30688b4e1ade8f1
Source dataset
uspto-grants-1994_04
Patent number
US05302748

Reaction notes

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