3-(Trifluoromethyl)phenol → HCID 70618386, compound

HRID 1704120Notes

Reaction equation

HRID 1704120 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C[O-].[Na+].Br[CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:23][CH:22]=1)[C:17]([O:19]C)=[O:18].[OH-].[K+].[CH:39]([NH:42][CH:43]([CH3:45])[CH3:44])([CH3:41])[CH3:40]>C1C=CC=CC=1.CCOCC.CCCCCC.C(O)C.O.CO>[CH:39]([NH:42][CH:43]([CH3:45])[CH3:44])([CH3:41])[CH3:40].[F:1][C:2]([F:10])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH:16]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][O:29][C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)=[CH:25][CH:26]=2)[C:17]([OH:19])=[O:18])[CH:4]=1

Participants

11

Reactant 5

HCID 73763-(Trifluoromethyl)phenolHCID 7912DiisopropylamineHCID 14797Potassium HydroxideHCID 10942334Sodium MethoxideHCID 54271297HCID 54271297, compound

Product 1

HCID 70618386HCID 70618386, compound

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolventHCID 19096565Water ethanolSolvent

Procedure

To a solution of 4.05 g of m-trifluoromethylphenol, 40 ml of methanol and 1.19 g of sodium methoxide is added 7.71 g of methyl bromo{p-[(p-chlorophenoxy)methoxy]phenyl}acetate in 10 ml of benzene. The mixture is refluxed for 21 hours and the solvent removed under reduced pressure. The residue is triturated with dichloromethane, filtered and the filtrate chromatographed on a column of silica gel (eluent methylene chloride). The main fraction is collected and the solvent removed under reduced pressure to give an oil. The above oil is combined with 4.0 g of potassium hydroxide, 75 ml of ethanol:water (9:1) and the mixture is refluxed for 4 hours. The mixture is concentrated under reduced pressure, diluted with water and acidified with concentrated HCl. The mixture is extracted with dichloromethane, the extract is dried (MgSO4) and the solvent removed under reduced pressure to give an oil. The above oil is dissolved in ether, diisopropylamine is added and the solution is diluted with hexane. Chilling and filtering gives 6.75 g of product as off-white crystals, mp 95°-100° C.

Workup

  1. temperatureThe mixture is refluxed for 21 hours
  2. customthe solvent removed under reduced pressure
  3. customThe residue is triturated with dichloromethane
  4. filtrationfiltered
  5. customthe filtrate chromatographed on a column of silica gel (eluent methylene chloride)
  6. customThe main fraction is collected
  7. customthe solvent removed under reduced pressure
  8. customto give an oil
  9. temperaturethe mixture is refluxed for 4 hours
  10. concentrationThe mixture is concentrated under reduced pressure
  11. additiondiluted with water
  12. extractionThe mixture is extracted with dichloromethane
  13. dry with materialthe extract is dried (MgSO4)
  14. customthe solvent removed under reduced pressure
  15. customto give an oil
  16. temperatureChilling
  17. filtrationfiltering

Sources & evidence

ORD record
ord-bf2a6e2ab99744f39d05cfbf74ea79dc
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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