O-Cresol → 4,4'-(9H-Fluorene-9,9-diyl)bis(2-methylphenol)

HRID 78961

Reaktionsgleichung

Reaktionsgleichung von HRID 78961
[C:1]1(=O)[C:13]2[C:5]([C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][CH:3]=[CH:2]1.[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22].[OH-:23].[Na+]>C(S)CCCCCCCCCCC>[OH:22][C:17]1[CH:18]=[CH:19][C:20]([C:13]2([C:1]3[CH:2]=[CH:3][C:6]([OH:23])=[C:5]([CH3:13])[CH:4]=3)[C:5]3[CH:4]=[CH:9][CH:8]=[CH:7][C:6]=3[C:11]3[C:12]2=[CH:1][CH:2]=[CH:3][CH:10]=3)=[CH:21][C:16]=1[CH3:15]

Komponenten

5

Edukt 3

HCID 335O-CresolHCID 14798Sodium HydroxideHCID 22281833Fluoreneone2×

Produkt 1

HCID 110143454,4'-(9H-Fluorene-9,9-diyl)bis(2-methylphenol)Ausbeute 813,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 81951-DodecanethiolKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A reaction was carried out by (a) feeding 23.0 g of fluorenone, 0.4 g of dodecyl mercaptan, 276.0 g of 2-methyl phenol, and 17.5 g of Nafion (registered trademark) NR50 (perfluorosulfonic acid cation-exchange resin manufactured by DuPont) into a 500 ml glass reactor vessel equipped with a stirrer, a condenser and a thermometer, and (b) stirring a mixture at 95° C. for 8 hours. The amount of remaining fluorenone was determined by HPLC, and found to be 0.1% or less. The ion exchange resin was removed by filtration to obtain a reaction mixture liquid. To the reaction mixture liquid thus obtained, 0.5 g of 29% sodium hydroxide aqueous solution was added, and thereafter 95.0 g of 2-methyl phenol was distilled away from an organic phase by concentration under reduced pressure. To an obtained concentrated liquid, 161 g of toluene and 23 g of water were added, and the mixture liquid was stirred at 80° C. Thereafter, an aqueous phase was separated and removed, and a target substance partitioned in the organic phase was recovered. The organic phase was further washed twice with 23 g of water, and cooled to 10° C. Then, precipitated crystals were subjected to filtration and drying to obtain 38.5 g of 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (yield: 85.7%, LC purity: 99.5%). Obtained 9,9-bis(4-hydroxy-3-methylphenyl)fluorene was dissolved by heat at 230° C. for 2 hours. The 9,9-bis(4-hydroxy-3-methylphenyl)fluorene thus dissolved show a hue of 2 in Gardner. The total amount of toluene used in the production was 4.2 parts by weight relative to 1 part by weight of the 9,9-bis(4-hydroxy-3-methylphenyl)fluorene.

Aufarbeitung

  1. customequipped with a stirrer, a condenser
  2. customThe ion exchange resin was removed by filtration
  3. customto obtain a reaction mixture liquid
  4. customTo the reaction mixture liquid thus obtained
  5. distillation95.0 g of 2-methyl phenol was distilled away from an organic phase by concentration under reduced pressure
  6. concentrationTo an obtained concentrated liquid, 161 g of toluene and 23 g of water
  7. additionwere added
  8. customThereafter, an aqueous phase was separated
  9. customremoved
  10. customa target substance partitioned in the organic phase
  11. customwas recovered
  12. washThe organic phase was further washed twice with 23 g of water
  13. temperaturecooled to 10° C
  14. customThen, precipitated crystals
  15. filtrationwere subjected to filtration
  16. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-64d0fb2deb274347a258b2cfb90d5780
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841491B2

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