Toluene → HCID 86657291, compound

HRID 1797816Notes

Reaction equation

HRID 1797816 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH:13]12CC(C=C1)CC2CO.C1(C)C=CC=CC=1>[OH-].C([O-])(=O)C.[Zr+4].C(OCC)(=O)C>[CH:2]12[CH2:6][CH:5]([CH:4]=[CH:3]1)[CH2:11][CH2:12]2.[CH3:13][C:4]1[CH:3]=[C:2]([F:1])[CH:12]=[CH:11][C:5]=1[CH:6]=[CH:7][C:8]([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 1140TolueneHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanolHCID 980703-(4-Fluorophenyl)-2-propenoic acid

Product 1

HCID 86657291HCID 86657291, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 86657292HCID 86657292, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
145 °C

Procedure

10 g (60 mmol) of 4-fluoro-cinnamic acid, 7.45 g (60 mmol) of 5-norbornene-2-methanol, and 0.3 g (0.02 eq.) of zirconium(IV) acetate hydroxide were added to 50 ml of toluene 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 with 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: 68%, Purity (GC): 92%)

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 with 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-4417e4d179f44196bb9f2cbae47cac32
Source dataset
uspto-grants-2013_01
Patent number
US08343597B2

Reaction notes

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