p-Anisoyl chloride → HCID 67863489, compound

HRID 1089369Notes

Reaction equation

HRID 1089369 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.[C:26]([O:29][CH2:30]C)(=[O:28])C>[N+](C1C=CC=CC=1)([O-])=O>[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:26]([O:29][CH3:30])=[O:28])[CH:5]=[CH:4][C:3]=2[O:2][CH3:1])=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8857Ethyl AcetateHCID 300018Methyl 3-(4-methoxyphenyl)propanoate

Product 1

HCID 67863489HCID 67863489, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

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 dissolved in nitrobenzene (200 ml). To the ice-chilled solution, A1C13 (26.7 g, 200.3 mmol) was added in 6 portions with vigorous stirring over a period of 3 hours. After all portions of A1C13 were added, stirring was continued for an additional 1 hour. The reaction mixture was poured into a beaker 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. additionA1C13 (26.7 g, 200.3 mmol) was added in 6 portions
  2. additionAfter all portions of A1C13 were added
  3. stirringstirring
  4. waitwas continued for an additional 1 hour
  5. additionThe reaction mixture was poured into a beaker
  6. additioncontaining
  7. additiona mixture of ice and 120 ml of 1N CHl
  8. stirringstirred vigorously
  9. customThe mixture was transferred into a separating funnel
  10. stirringwhich was shaken well
  11. washThe organic layer in the solution was washed twice with a saturated aqueous solution of sodium bicarbonate
  12. dry with materialAfter drying over unhydrous sodium sulfate
  13. customthe solvent was removed in vacuo
  14. customThe residue was purified by flash column chromatography
  15. customto produce a pale yellow oil

Sources & evidence

ORD record
ord-26dffab81f5b407ea7c17c1956254d6f
Source dataset
uspto-grants-1990_10
Patent number
US04965405

Reaction notes

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