Diphenyl Ether → HCID 59861577, compound

HRID 1672090Notes

Reaction equation

HRID 1672090 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([NH:12][CH:13]=[C:14]([C:20]([O:22]CC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][CH:11]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>CCO>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:7]=[C:8]2[C:9]([C:20](=[O:22])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][NH:12]2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 59861574HCID 59861574, compound

Product 1

HCID 59861577HCID 59861577, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
257.5 °C

Procedure

Compound 7 was added to 300 mL diphenyl ether (Aldrich) that had been preheated to 250° C. in a 1 L 3-neck round bottom flask. The temperature dropped to ca 240° C. for a brief time (1-2 min), after which it was brought up to 257° C. and maintained at 255-260° C. for 15 min, as the color darkened and evolution of EtOH vapor was observed. Upon cooling to room temperature, some ppt separated, but the mixture was extremely thick. The mixture was diluted 1:4 with hexane, and more ppt separated. The ppt was filtered, washed 3× hexane, and dried to afford 19.02 g product (84%) 8. Analysis (1H NMR) showed that the product was of high enough purity to be used as such in the next step.

Workup

  1. customhad been preheated to 250° C. in a 1 L 3-neck round bottom flask
  2. additionThe temperature dropped to ca 240° C. for a brief time (1-2 min)
  3. customwas brought up to 257° C.
  4. temperatureUpon cooling to room temperature
  5. customsome ppt separated
  6. additionThe mixture was diluted 1:4 with hexane, and more ppt separated
  7. filtrationThe ppt was filtered
  8. washwashed 3× hexane
  9. customdried

Sources & evidence

ORD record
ord-5f154507d6654268af24f45569e79338
Source dataset
uspto-grants-2011_08
Patent number
US07998462B2

Reaction notes

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