HCID 22155199, compound → HCID 22155255, compound

HRID 2232740Notes

Reaction equation

HRID 2232740 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)(O)[CH2:8][C:9]#[N:10])=[CH:3][CH:2]=1.CO>FC(F)(F)C(O)=O>[C:15]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:14]=[CH:13][C:12]([C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:2][CH:3]=2)=[CH:8][C:9]#[N:10])=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 22155199HCID 22155199, compound

Product 1

HCID 22155255HCID 22155255, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
65 °C

Procedure

The crude carbinol 3,3-bis[(1,1-biphenyl)-4-yl]-3-hydroxypropanenitrile (13.5 g; 0.036 mol) was dissolved in trifluoroacetic acid (30 mL) and the solution was heated at 65° C. for 10 min. After the solvent was removed in vacuo, the residue was triturated with water and the resulting solids were dissolved in dichloromethane. The dried (MgSO4) solution was evaporated to provide 12.2 g of 3,3-bis[(1,1'-biphenyl)-4-yl]-2-propenenitrile as an oil that was contaminated with a small amount of starting ketone.

Workup

  1. customAfter the solvent was removed in vacuo
  2. customthe residue was triturated with water
  3. dissolutionthe resulting solids were dissolved in dichloromethane
  4. dry with materialThe dried (MgSO4) solution
  5. customwas evaporated

Sources & evidence

ORD record
ord-70bbda8b223f4a6bb8fb1243c045656b
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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