O-Xylene → HCID 86657294, compound

HRID 1797818Notes

Reaction equation

HRID 1797818 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].[CH:14]12CC(C=C1)CC2CO.C1(C)C(C)=CC=CC=1>[OH-].C([O-])(=O)C.[Zr+4].C(OCC)(=O)C>[CH:12]12[CH2:5][CH:4]([CH:3]=[CH:2]1)[CH2:10][CH2:11]2.[CH3:14][C:3]1[C:2]([F:1])=[C:12]([F:13])[CH:11]=[CH:10][C:4]=1[CH:5]=[CH:6][C:7]([O-:9])=[O:8]

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanolHCID 1454863-(3,4-Difluorophenyl)prop-2-enoic acid

Product 1

HCID 86657294HCID 86657294, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 86657292HCID 86657292, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
145 °C

Procedure

5 g (27.2 mmol) of 3,4-di-fluoro-cinnamic acid, 3.38 g (1 eq.) of 5-norbornene-2-methanol, and 0.13 g (0.02 eq.) of zirconium(IV) acetate hydroxide were added to 50 ml of xylene and stirred. The mixture was heated to 145° C. under N2 atmosphere and azeotropically refluxed for 24 hours. After the reaction, the mixture cooled down to room temperature and was added with 100 volume % of ethyl acetate. The resulting product was extracted by 1M HCl and washed again with water. The organic layer was dried with Na2SO4 and the solvent was evaporated out to give a highly viscous material. (Yield: 63%, Purity (GC): 80%)

Workup

  1. temperatureazeotropically refluxed for 24 hours
  2. customAfter the reaction
  3. temperaturethe mixture cooled down to room temperature
  4. extractionThe resulting product was extracted by 1M HCl
  5. washwashed again with water
  6. dry with materialThe organic layer was dried with Na2SO4
  7. customthe solvent was evaporated out
  8. customto give a highly viscous material

Sources & evidence

ORD record
ord-b743269aac2642f9b3b687f5699031a3
Source dataset
uspto-grants-2013_01
Patent number
US08343597B2

Reaction notes

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