3-Bromo-1-propanol → HCID 13796792, compound

HRID 1906699Notes

Reaction equation

HRID 1906699 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)#[N:7].[OH-].[K+]>C(O)C.O>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:2][CH2:3][CH2:4][OH:5])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)#[N:7]

Participants

6

Reactant 3

HCID 123083-Bromo-1-propanolHCID 14797Potassium HydroxideHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 13796792HCID 13796792, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-Bromo-1-propanol (5.6 g, 0.04 mol) and 4-cyano-4'-hydroxybiphenyl (6.0 g, 0.02 mol) were dissolved in ethanol (300 ml) and agitated at room temperature. To this solution was gradually dropwise added a solution of KOH (10 g) dissolved in water (20 ml), over 30 minutes, followed by stirring for 40 hours, distilling off about 200 ml of ethanol under reduced pressure, adding water (500 ml) to deposit solids, adding toluene (300 ml) to the mixture system, filtering off insoluble matter, washing the toluene solution twice with 2N-NaOH, then three times with water, drying over anhydrous sodium sulfate, distilling off toluene, and recrystallizing the resulting crystals from methanol to obtain 4-cyano-4'-(3-hydroxypropoxy)biphenyl. Yield: 2 g (28%). C-N: 109.0°-110.7° C. N-I: 113.6° C.

Workup

  1. stirringby stirring for 40 hours
  2. distillationdistilling off about 200 ml of ethanol under reduced pressure
  3. additionadding water (500 ml)
  4. additionadding toluene (300 ml) to the mixture system
  5. filtrationfiltering off insoluble matter
  6. washwashing the toluene solution twice with 2N-NaOH
  7. dry with materialthree times with water, drying over anhydrous sodium sulfate
  8. distillationdistilling off toluene
  9. customrecrystallizing the resulting crystals from methanol

Sources & evidence

ORD record
ord-91722884a37a409a846d22ffc8023454
Source dataset
uspto-grants-1987_03
Patent number
US04654162

Reaction notes

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