4,4'-Dihydroxybiphenyl → 4,4'-Dibutoxybiphenyl

HRID 1611570Notes

Reaction equation

HRID 1611570 reaction equation
[Na].S([CH2:6][CH2:7][CH2:8][CH2:9]OC1C=CC=CC=1C1C=CC(S(O)(=O)=O)=CC=1)(O)(=O)=O.[OH:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=2)=[CH:30][CH:29]=1.Br[CH2:42][CH2:43][CH2:44][CH3:45].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:6]([O:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:36][CH:35]=2)=[CH:32][CH:33]=1)[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 71124,4'-DihydroxybiphenylHCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 131725261HCID 131725261, compound

Product 1

HCID 6043124,4'-Dibutoxybiphenyl

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In the same manner as in (1) above, 4,4′-dihydroxybiphenyl, 1-bromobutane and potassium carbonate were reacted in a proportion of 1:6:6 to prepare the objective compound. The reaction was conducted by heating under reflux at the refluxing temperature of acetone for 6 hours. The reaction solution thus obtained was cooled, potassium carbonate was filtered off, the filtrate was concentrated under reduced pressure and put into water, and the precipitate thus formed was collected by filtration and recrystallized from ethanol to obtain 4,4′-dibutoxybiphenyl.

Workup

  1. customto prepare the objective compound
  2. temperatureby heating
  3. customThe reaction solution thus obtained
  4. temperaturewas cooled
  5. filtrationpotassium carbonate was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe precipitate thus formed
  8. filtrationwas collected by filtration
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d4ea638fdfe44f94857a8c253751cac2
Source dataset
uspto-grants-2006_01
Patent number
US06989212B2

Reaction notes

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