Benzene → HCID 13037779, compound

HRID 1156631Notes

Reaction equation

HRID 1156631 reaction equation
C[O-].[Na+].C1CCC([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])CC1.[C:19]([O:25][CH3:26])(=[O:24])[C:20]([O:22]C)=O.Cl.[CH:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O.CCOCC>[CH:28]1([C:16]2[CH:17]=[CH:18][C:13]([C:11](=[O:12])[CH2:10][C:20](=[O:22])[C:19]([O:25][CH3:26])=[O:24])=[CH:14][CH:15]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

8

Reactant 5

HCID 241Benzene2×HCID 313Hydrochloric AcidHCID 11120Dimethyl oxalateHCID 10921586HCID 10921586, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 13037779HCID 13037779, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 22 ml of dry benzene there was added, under nitrogen atmosphere, 1.68 g (31.2 mMol) of sodium methoxide. There was then slowly added with stirring a solution of 6.06 g (30 mMol) of the 4-cyclohexyl acetophenone prepared in Step A above and 3.54 g (30 mMol) of freshly recrystallized dimethyl oxalate in 40 ml of benzene. The reaction mixture was cooled and soon after addition a yellow crystalline precipitate formed. The reaction mixture was allowed to warm to room temperature and stirred for an additional hour. There was then added 75 ml of ether and 24 ml of 2 N hydrochloric acid with 6 ml of water. The mixture was shaken for about 15 minutes, until all of the solid dissolved. The organic layer was then separated, washed with a small amount of water, and dried over magnesium sulfate. The solvent was then evaporated, the residue partially crystallized on cooling, and then crystallized from 3:1 petroleum ether:benzene. After cooling, 3.33 g of yellow solid product, m.p. 96°-98° C., was filtered off.

Workup

  1. additionThere was then slowly added
  2. temperatureThe reaction mixture was cooled
  3. additionsoon after addition a yellow crystalline precipitate
  4. customformed
  5. stirringThe mixture was shaken for about 15 minutes
  6. dissolutionuntil all of the solid dissolved
  7. customThe organic layer was then separated
  8. washwashed with a small amount of water
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was then evaporated
  11. customthe residue partially crystallized
  12. temperatureon cooling
  13. customcrystallized from 3:1 petroleum ether
  14. temperatureAfter cooling
  15. filtration3.33 g of yellow solid product, m.p. 96°-98° C., was filtered off

Sources & evidence

ORD record
ord-b245dfba4538414680f42d2ba7b4f4b3
Source dataset
uspto-grants-1982_06
Patent number
US04336397

Reaction notes

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