Potassium Carbonate → HCID 20090721, compound

HRID 274154Notes

Reaction equation

HRID 274154 reaction equation
[CH2:1]([O:7][C:8]1[CH:9]=[C:10](C2C(O)=CC=CC=2)[C:11](O)=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:22](=[O:25])([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][Br:35]>CC(C)=O>[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:3]2[CH:4]=[CH:5][C:22]([O:25][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][Br:35])=[CH:1][CH:2]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 20090726HCID 20090726, compound

Product 1

HCID 20090721HCID 20090721, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4'-(hexyloxy)biphenol (8.10 g, 30 mmol), potassium carbonate (8.30 g, 60 mmol), 1,6-dibromohexane (22.0 g, 90 mmol) and acetone (80 mL) was heated to reflux for 24 h. One-half the acetone was removed by distillation and the mixture was poured into tetrahydrofuran:ether, 1:1 (600 mL), and washed with water. The solution was dried over magnesium sulfate and concentrated to a solid. The solid was recrystallized from tetrahydrofuran-ether to give 4'-(hexyloxy)-4-(6-bromohexyloxy)biphenyl (5.0 g, 38%): mp 103-105° C.; NMR 7.4(d, 4H), 6.85(d, 4H), 3.92(t, 4H), 3.4(t, 2H), 2.0-1.2(m, 16H), 0.9(t, 3H).

Workup

  1. temperatureto reflux for 24 h
  2. customOne-half the acetone was removed by distillation
  3. additionthe mixture was poured into tetrahydrofuran
  4. washether, 1:1 (600 mL), and washed with water
  5. dry with materialThe solution was dried over magnesium sulfate
  6. concentrationconcentrated to a solid
  7. customThe solid was recrystallized from tetrahydrofuran-ether

Sources & evidence

ORD record
ord-8807ebf57025487fbb42a9153413db74
Source dataset
uspto-grants-1995_02
Patent number
US05389285

Reaction notes

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