Water → HCID 57589645, compound

HRID 2204775Notes

Reaction equation

HRID 2204775 reaction equation
[O:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][C:5](O)=[CH:4][CH:3]=1.[C:16](=[O:19])([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].O>CN(C=O)C>[O:1]([C:2]1[CH:7]=[CH:6][C:5]([O:19][CH2:16][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:4][CH:3]=1)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 160694,4'-Dihydroxydiphenyl ether

Product 1

HCID 57589645HCID 57589645, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,4′-oxydiphenol (4,4′-dihydroxydiphenyl ether) (1 eq, 10 g, 49.5 mmol), potassium carbonate (2.5 eq, 17.1029 g, 123.75 mmol, 138.205 g/mol), and 1-bromoheptane (2.5 eq, 22.1636 g, 19.5 mL, 123.75 mmol, 179.10 g/mol, d=1.14 g/mL) were dissolved in DMF (100 mL) at 80° C. The reaction was stirred until complete as determined by TLC. The reaction was poured into water and filtered. The crude product was taken up in methanol and heated while stirring, followed by sonication. The suspension was then filtered warm and the product washed with room temperature methanol to yield a white powder (compound characterized by Structure A: 4,4′-oxybis((heptyloxy)benzene)). The yield was 16.3 g (83.6%).

Workup

  1. filtrationfiltered
  2. temperatureheated
  3. stirringwhile stirring
  4. customfollowed by sonication
  5. filtrationThe suspension was then filtered
  6. temperaturewarm
  7. washthe product washed with room temperature methanol

Sources & evidence

ORD record
ord-239e0e0c472a4d98b188e62c76460634
Source dataset
uspto-grants-2016_06
Patent number
US09366661B1

Reaction notes

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