Triphenylcarbinol → 1,4-PHENYLENE-4,4'-BIS(2,6-DIPHENYL-4-PYRYLIUM TETRAFLUOROBORATE)

HRID 1199276Notes

Reaction equation

HRID 1199276 reaction equation
[CH:1]1[C:6](C=O)=[CH:5][CH:4]=[C:3]([CH:9]=[O:10])[CH:2]=1.[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])[CH3:12].[OH-].[K+].[H+].[B-:23]([F:27])([F:26])([F:25])[F:24].C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)O)C=CC=CC=1.O=[C:49]([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)[CH2:50][CH:51]([C:61]1[CH:66]=[CH:65][C:64]([CH:67](CC(C2C=CC=CC=2)=O)[CH2:68][C:69]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)=O)=[CH:63][CH:62]=1)[CH2:52]C(=O)C1C=CC=CC=1>C(O)C.O.C(OC(=O)C)(=O)C>[F:24][B-:23]([F:27])([F:26])[F:25].[F:24][B-:23]([F:27])([F:26])[F:25].[C:61]1([C:51]2[CH:50]=[C:49]([C:86]3[CH:87]=[CH:88][CH:89]=[CH:90][CH:91]=3)[O+:10]=[C:9]([C:3]3[CH:2]=[CH:1][CH:6]=[CH:5][CH:4]=3)[CH:52]=2)[CH:62]=[CH:63][C:64]([C:67]2[CH:68]=[C:69]([C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)[O+:13]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=2)=[CH:65][CH:66]=1

Participants

10

Reactant 6

HCID 6457TriphenylcarbinolHCID 7410AcetophenoneHCID 12173TerephthalaldehydeHCID 14797Potassium HydroxideHCID 28118Tetrafluoroboric acidHCID 3301951AE-018/31863049

Product 1

HCID 118286521,4-PHENYLENE-4,4'-BIS(2,6-DIPHENYL-4-PYRYLIUM TETRAFLUOROBORATE)

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

4,4'-(1,4-Phenylene)bis(2,6-diphenylpyrylium) bis(tetrafluoroborate) was prepared as follows: To a solution of terephthaldehyde (0.40 mol) and acetophenone (2.4 mol) in ethanol (1.2L) was added a solution of potassium hydroxide (0.50 mol) in water (100mL). The solution was heated at reflux for 24 hours. The product, 1,4-bis(1,5-dioxo-1,5-diphenylpentan-3-yl)benzene, was collected by filtration, washed with ethanol (1L), and dried. Fluoboric acid (0.11 mol) was added over a 30 minute period to a solution of triphenylmethanol (0.11 mol) in acetic anhydride (500 mL). Stirring was continued for 2 hours after addition was complete, then 1,4-bis(1,5-dioxo-1,5-diphenylpentan-3-yl)benzene (0.05 mol) was added and the mixture heated at reflux for 1 hour. The reaction mixture was cooled to room temperature, filtered, and the collected bis(pyrylium) salt was washed with acetone (250 mL) and dried at 50° C. at reduced pressure overnight.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe product, 1,4-bis(1,5-dioxo-1,5-diphenylpentan-3-yl)benzene, was collected by filtration
  4. washwashed with ethanol (1L)
  5. customdried
  6. additionafter addition
  7. temperaturethe mixture heated
  8. temperatureat reflux for 1 hour
  9. filtrationfiltered
  10. washthe collected bis(pyrylium) salt was washed with acetone (250 mL)
  11. customdried at 50° C. at reduced pressure overnight

Sources & evidence

ORD record
ord-5635f328a71c48e793f80590e8bd5d0d
Source dataset
uspto-grants-1990_02
Patent number
US04898923

Reaction notes

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