Ethylene carbonate → 4-(2-Hydroxyethoxyphenyl)fluorene

HRID 789

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.

Workup

temperatureat reflux
customthe solvent was decanted from the precipitated product
washThe resulting white solid was washed with ligroin (
customdried under a stream of nitrogen
customThe product was recrystallized from methanol

Sources & evidence

ORD record: ord-bfcf42b524d14d69860f018538be3094
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723264

Linked notes

Loading…