Ethylene carbonate → 4-(2-Hydroxyethoxyphenyl)fluorene

Reaction equation

OC1[CH:7]=[CH:6][C:5]([C:8]2([C:21]3[CH:26]=CC(O)=CC=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3C2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:4]C=1.C1(=O)O[CH2:31][CH2:30][O:29]1.[C:34](=[O:37])([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>>[OH:29][CH2:30][CH2:31][O:37][C:34]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[C:15]1[C:20]2[C:8]3[C:5](=[CH:6][CH:7]=[CH:26][CH:21]=3)[CH2:4][C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

Reactant 4

HCID 7303Ethylene carbonate

HCID 11430Potassium Carbonate

HCID 2855718-Crown-6

HCID 767169,9-Bis(4-hydroxyphenyl)fluorene

Product 1

HCID 232084214-(2-Hydroxyethoxyphenyl)fluoreneYield 970.1%

Procedure

A mixture of 84.4 g (0.241 mol) of 9,9-bis(4-hydroxyphenyl)fluorene, 46.7 g (0.53 mol) of ethylene carbonate, 3.3 g (0.024 mol) of potassium carbonate, and a catalytic amount of 18-crown-6 in 400 mL of xylenes was heated at reflux with mechanical stirring for 6 h. The mixture was allowed to cool slowly to room temperature, and the solvent was decanted from the precipitated product. The resulting white solid was washed with ligroin (to prevent the formation of a gummy mass), and dried under a stream of nitrogen. The product was recrystallized from methanol, providing 70.4 g (67%) of a white powder.