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

HRID 78962Notes

Reaction equation

HRID 78962 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:8].[Na+]>O>[OH:8][C:2]1[CH:3]=[CH:4][C:5]([C:7]2([C:5]3[CH:4]=[CH:3][C:2]([OH:8])=[C:1]([CH3:7])[CH:6]=3)[C:6]3[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=3[C:6]3[C:1]2=[CH:2][CH:3]=[CH:4][CH:5]=3)=[CH:6][C:1]=1[CH3:7]

Participants

4

Reactant 2

HCID 1140TolueneHCID 14798Sodium Hydroxide

Product 1

HCID 110143454,4'-(9H-Fluorene-9,9-diyl)bis(2-methylphenol)Yield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A reaction was carried out in the same manner as in Example 3. To an obtained reaction mixture liquid, 135 g of toluene, 23 g of water, and 17.9 g of 29% sodium hydroxide aqueous solution were added, and the reaction mixture liquid was neutralized by stirring at 80° C. Thereafter, an aqueous phase was separated and removed. An organic phase was further washed twice with 23 g of water. From the organic phase, toluene and 91.5 g of 2-methyl phenol were distilled away by concentration under reduced pressure. Thereafter, 161 g of toluene was added to a concentrated liquid, and the mixture liquid was cooled to 10° C. Then, precipitated crystals were subjected to filtration and drying to obtain 37.0 g of 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (yield: 82.5%, LC purity: 98.7%). 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 4 in Gardner. The total amount of toluene used in the production was 8 parts by weight relative to 1 part by weight of the 9,9-bis(4-hydroxy-3-methylphenyl)fluorene.

Workup

  1. additionwere added
  2. customThereafter, an aqueous phase was separated
  3. customremoved
  4. washAn organic phase was further washed twice with 23 g of water
  5. distillationFrom the organic phase, toluene and 91.5 g of 2-methyl phenol were distilled away by concentration under reduced pressure
  6. additionThereafter, 161 g of toluene was added to a concentrated liquid
  7. temperaturethe mixture liquid was cooled to 10° C
  8. customThen, precipitated crystals
  9. filtrationwere subjected to filtration
  10. customdrying

Sources & evidence

ORD record
ord-dcd4c6fe88cf4889b2e8c699ff0550cb
Source dataset
uspto-grants-2014_09
Patent number
US08841491B2

Reaction notes

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