Hydrochloric Acid → 3-{3-[4-Acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]propoxy}-nitrobenzene

HRID 620305Notes

Reaction equation

HRID 620305 reaction equation
[H-].[Na+].[C:3]([C:6]1[CH:25]=[CH:24][C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:19][CH:20]=2)=[C:8]([CH2:26][CH2:27][C:28]([F:31])([F:30])[F:29])[C:7]=1[OH:32])(=[O:5])[CH3:4].[CH3:33]I.Cl>CN(C)C=O>[C:3]([C:6]1[CH:25]=[CH:24][C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:19][CH:20]=2)=[C:8]([CH2:26][CH2:27][C:28]([F:29])([F:31])[F:30])[C:7]=1[O:32][CH3:33])(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 198186533-{3-[4-Acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-nitrobenzene

Product 1

HCID 198186143-{3-[4-Acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]propoxy}-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,530 mg of sodium hydride are added to a solution of 7.46 g of 3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-nitrobenzene in 75 ml of dimethylformamide and the reaction mixture is warmed to 40°. 5.7 g of methyl iodide are added dropwise in the course of 15 minutes. Thereafter, the reaction mixture is kept at 40° C. for a further hour. After cooling, it is poured onto dilute hydrochloric acid and extracted with methylene chloride and the extract is evaporated. Recrystallisation from ether/hexane gives 3-{3-[4-acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-nitrobenzene.

Workup

  1. temperaturethe reaction mixture is warmed to 40°
  2. waitThereafter, the reaction mixture is kept at 40° C. for a further hour
  3. temperatureAfter cooling
  4. extractionextracted with methylene chloride
  5. customthe extract is evaporated
  6. customRecrystallisation from ether/hexane

Sources & evidence

ORD record
ord-62aa2f91f04e4ddfa0b2b4e7e6e74db8
Source dataset
uspto-grants-1989_04
Patent number
US04820726

Reaction notes

Loading…