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

Participants

Reaction Conditions

Reaction Steps

A reaction was carried out by (a) feeding 23 g of fluorenone, 0.57 g of tungstophosphoric acid, and 161 g of 2-methyl phenol into a 500 ml glass reactor vessel equipped with a stirrer, a condenser and a thermometer, and (b) stirring a mixture under a reduced pressure of 1.3×103 Pa at 70° C. for 4 hours while removing generated water out of the system. The amount of remaining fluorenone was determined by HPLC, and found to be 0.1% or less. To an obtained reaction mixture liquid, 0.6 g of 29% sodium hydroxide aqueous solution was added, and 103.5 g of 2-methyl phenol was recovered from an organic phase by concentration under reduced pressure. To a concentrated liquid, 161 g of toluene and 46 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 an organic phase was recovered. The organic phase was further washed twice with 46 g of water, and cooled to 10° C. Then, precipitated crystals were subjected to filtration and drying to obtain 40.3 g of 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (yield: 83.5%, LC purity: 99.3%). 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 1 or less in Gardner. The total amount of toluene used was 4 parts by weight relative to 1 part by weight of the 9,9-bis(4-hydroxy-3-methylphenyl)fluorene.

Provenance & Evidence