4-Hydroxybiphenyl → HCID 746627, compound

HRID 2060574Notes

Reaction equation

HRID 2060574 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+]([C:17]1[CH:18]=[C:19]([C:25]#[N:26])[C:20](=[CH:23][CH:24]=1)[C:21]#[N:22])([O-])=O.C(=O)([O-])[O-].[K+].[K+]>Cl>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([O:13][C:17]3[CH:18]=[C:19]([C:25]#[N:26])[C:20](=[CH:23][CH:24]=3)[C:21]#[N:22])=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 746627HCID 746627, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A 1 L round 3-necked round-bottomed flask was charged with 4-phenylphenol (45.7 g, 0.27 mole), 4-nitrophthalonitrile (50 g, 0.29 mole), potassium carbonate (51.9 g, 0.38 mole), and dimethylformide (470 mL). The resulting solution was heated under nitrogen with stirring to 90° C. for 1.5 hour (progress of reaction can be monitored by TLC). The dark brown reaction mixture was then poured into 2M aqueous HCl solution (300 mL) with stirring. The product precipitated out as a pale brown powder. The powder was collected by filtration and dried in a vacuum oven at 150° C. to give the desired product (71 g, 94% yield). 1H NMR (δ, D6-DMSO): 8.13 (d, 1H), 7.87 (d, 1H), 7.80 (d, 2H), 7.70 (d, 2H), 7.55-7.35 (m, 4H), 7.30 (d, 2H).

Workup

  1. temperatureThe resulting solution was heated under nitrogen
  2. custom(progress of reaction can be monitored by TLC)
  3. stirringwith stirring
  4. customThe product precipitated out as a pale brown powder
  5. filtrationThe powder was collected by filtration
  6. customdried in a vacuum oven at 150° C.

Sources & evidence

ORD record
ord-aa7c2acd05b541c1b0d1ca71661877a4
Source dataset
uspto-grants-2012_10
Patent number
US08278383B2

Reaction notes

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