Water → HCID 1564178, compound

HRID 974022Notes

Reaction equation

HRID 974022 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.[H-].[Na+].Cl[CH2:17][C:18]#[N:19].O>CN(C=O)C>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[CH:9][C:10]([O:13][CH2:17][C:18]#[N:19])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 71034-HydroxybiphenylHCID 7856ChloroacetonitrileHCID 24758Sodium hydride

Product 1

HCID 1564178HCID 1564178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-phenylphenol (3.4 g, 20 mmol) in DMF (75 ml) was added sodium hydride (0.88 g of a 60% dispersion in oil, 22 mmol). The mixture was stirred at 70° C. under nitrogen until a clear solution was obtained, then cooled to 50° C. To the mixture was added chloroacetonitrile (1.5 ml, 24 mmol). A precipitate formed immediately. The mixture was cooled to room temperature, poured into water (300 ml), and extracted with ether. The ether extracts were dried (MgsO4), filtered and evaporated. Recrystallization of the residue from methanol provided [1,1'-biphenyl]-4yloxyacetonitrile, mp 81°-83° C.

Workup

  1. customwas obtained
  2. temperaturecooled to 50° C
  3. customA precipitate formed immediately
  4. temperatureThe mixture was cooled to room temperature
  5. extractionextracted with ether
  6. dry with materialThe ether extracts were dried (MgsO4)
  7. filtrationfiltered
  8. customevaporated
  9. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-171b308368d74d6e8acfa8041c20adf6
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

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