Ethylene Glycol → 1-(4-Biphenylyl)cyclopropanecarboxylic acid

HRID 2391044Notes

Reaction equation

HRID 2391044 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2([C:10]#N)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[OH-:18].[K+].C(O)C[OH:22]>O>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2([C:10]([OH:22])=[O:18])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 666605281-(Biphenyl-4-YL)-cyclopropanecarbonitrile

Product 1

HCID 215522631-(4-Biphenylyl)cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(Biphenyl-4-yl)cyclopropanecarbonitrile (63 g, 288 mmol), KOH (1130 mmol) and ethylene glycol (350 mL) were heated to 160° C. for 6 hours (reaction complete by LCMS). The solution was cooled to room temperature, water (1.5 L) was added and the solution acidified to precipitate the product. The product was filtered overnight on a large Buchner (product formed a gel like suspension). The resulting wet solid was extracted with CH2Cl2 (˜2 L) and water, dried and evaporated to yield ˜60 g of 1-(biphenyl-4-yl)cyclopropanecarboxylic acid that was used as such in the next step.

Workup

  1. custom(reaction complete by LCMS)
  2. customto precipitate the product
  3. filtrationThe product was filtered overnight on a large Buchner (product
  4. customformed a gel like suspension)
  5. extractionThe resulting wet solid was extracted with CH2Cl2 (˜2 L) and water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-ee07fb006f0644e08837a6c381599877
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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