Phenol → 4-Phenoxy-4'-phenylethynylbenzophenone

HRID 1757683Notes

Reaction equation

HRID 1757683 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:9]1[CH:30]=[CH:29][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1.C1(C)C=CC=CC=1>CC(N(C)C)=O>[O:7]([C:9]1[CH:30]=[CH:29][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 1140TolueneHCID 40956574-Fluoro-4'-(phenylethynyl)benzophenone

Product 1

HCID 193892734-Phenoxy-4'-phenylethynylbenzophenoneYield 96.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
23 °C

Procedure

A 100 mL flask equipped with nitrogen inlet, overhead stirring assembly, Dean-Stark trap, and reflux condenser was charged with phenol (0.35 g, 0.0038 mol), 4-fluoro-4'-phenylethynylbenzophenone (0.10 g, 0.0038 mol) potassium carbonate (0.39 g, 0.003 mol), 25 mL of toluene, and 50 mL of DMAc. The mixture was heated to reflux and water was removed by azeotropicdistillation, followed by the removal of toluene over a 20 hour period. Thereaction was cooled to 23° C., and the mixture was poured into 1 L of acidic (HCl) water. The precipitate was collected by filtration to afford 1.37 g (96%) of 4-phenoxy-4'-phenylethynylbenzophenone as a white powder: mp 165.5° C. IR (KBr): 2216 cm-1 (ethynyl), 1650 cm-1 (carbonyl): 1H-NMR (CDCl3): 7.8-6.8 pp, (m H aromatic). Anal Calcd. for C27H18O2: %C=86.61, %H=4.85. Found: %C=86.46, %H=4.68. The structure of this compound is given below: ##STR10##The DSC thermogram of this compound is presented in FIG. 3.

Workup

  1. customA 100 mL flask equipped with nitrogen inlet
  2. temperatureDean-Stark trap, and reflux condenser
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. customwater was removed by azeotropicdistillation
  6. customfollowed by the removal of toluene over a 20 hour period
  7. additionthe mixture was poured into 1 L of acidic (HCl) water
  8. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c83bcb6f493e497e8831001a723ce09e
Source dataset
uspto-grants-1995_08
Patent number
US05446204

Reaction notes

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