Hydrochloric Acid → HCID 14766294, compound

HRID 2396659Notes

Reaction equation

HRID 2396659 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].S(C1C=CC(C)=CC=1)(O[C@@H:13]([CH3:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=O)=O.C(=O)([O-])[O-].[K+].[K+].Cl>CCC(C)=O>[CH3:19][C@@H:13]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97072-FluorophenolHCID 11430Potassium CarbonateHCID 54517469HCID 54517469, compound

Product 1

HCID 14766294HCID 14766294, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A reaction vessel was charged with 10 g of 2-fluorophenol, 25 g of (S)-1-methylhexyl tosylate, 20 g of potassium carbonate and 160 ml of MEK, and the mixture was refluxed with stirring for 14 hours (the disappearance of the starting materials was confirmed by TLC). The reaction liquid was poured into diluted hydrochloric acid and the mixture was extracted with benzene. The extract was washed with water and dried over Glauber's salt, and the solvents were distilled off. The residue was distilled under reduced pressure to obtain 14 g (74.5%) of (R) -2- (1-methylhexyl) oxyfluorobenzene.

Workup

  1. temperaturethe mixture was refluxed
  2. customThe reaction liquid
  3. extractionthe mixture was extracted with benzene
  4. washThe extract was washed with water
  5. dry with materialdried over Glauber's salt
  6. distillationthe solvents were distilled off
  7. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-80f72c7f036d468da70de063588c7779
Source dataset
uspto-grants-1996_02
Patent number
US05494605

Reaction notes

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