Nitrobenzene → HCID 67863489, compound

HRID 729107Notes

Reaction equation

HRID 729107 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10]C(OC)=O)=[CH:5][CH:4]=1.[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.[N+](C1C=CC=CC=1)([O-])=O.[Al+3].[Cl-].[Cl-].[Cl-].[C:39]([O:42][CH2:43]C)(=[O:41])C>>[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([C:8]2[CH:7]=[C:6]([CH:9]([CH3:10])[C:39]([O:42][CH3:43])=[O:41])[CH:5]=[CH:4][C:3]=2[O:2][CH3:1])=[O:22])=[CH:19][CH:18]=1

Participants

6

Reactant 5

HCID 7416NitrobenzeneHCID 7477p-Anisoyl chlorideHCID 8857Ethyl AcetateHCID 300018Methyl 3-(4-methoxyphenyl)propanoateHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 67863489HCID 67863489, compound

Procedure

The methyl 3-(4-methoxyphenyl)propionate (10.8 g, 55.6 mmol) prepared in Example 1 and 4-methoxybenzoyl chloride (11.4 g, 66.8 mmol) were dissolvedin nitrobenzene (200 ml). To the ice-chilled solution, AlCl3 (26.7 g, 200.3 mmol) was added in 6 portions with vigorous stirring over a period of 3 hours. After all portions of AlCl3 were added, stirring was continued for an additional 1 hour. The reaction mixture was poured into abeaker containing a mixture of ice and 120 ml of 1N CHl and stirred vigorously. The mixture was transferred into a separating funnel, which was shaken well after the addition of ethyl acetate. The organic layer in the solution was washed twice with a saturated aqueous solution of sodium bicarbonate, then twice with a saturated aqueous solution of sodium chloride. After drying over unhydrous sodium sulfate, the solvent was removed in vacuo. The residue was purified by flash column chromatography using 30% ethyl acetate/hexane to produce a pale yellow oil.

Workup

  1. additionwas added in 6 portions
  2. stirringstirring
  3. waitwas continued for an additional 1 hour
  4. additionThe reaction mixture was poured into abeaker
  5. additioncontaining
  6. additiona mixture of ice and 120 ml of 1N CHl
  7. stirringstirred vigorously
  8. customThe mixture was transferred into a separating funnel
  9. stirringwhich was shaken well
  10. washThe organic layer in the solution was washed twice with a saturated aqueous solution of sodium bicarbonate
  11. dry with materialAfter drying over unhydrous sodium sulfate
  12. customthe solvent was removed in vacuo
  13. customThe residue was purified by flash column chromatography
  14. customto produce a pale yellow oil

Sources & evidence

ORD record
ord-2e454b7d7afb4b46b6f1099a0f2d421e
Source dataset
uspto-grants-1991_09
Patent number
US05051526

Reaction notes

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