1,2-Dichloroethane → 2,7-Bis(4-(6-acryloyloxyhexyl)oxybenzoyloxy)fluorene

HRID 2416362Notes

Reaction equation

HRID 2416362 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([OH:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1)(=[O:19])[CH:17]=[CH2:18].[CH2:37](Cl)[CH2:38]Cl.ClCCl>CN(C1C=CN=CC=1)C.O>[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:38]1[CH:37]=[CH:35][C:31]([C:32]([O:1][C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([O:15][C:32](=[O:33])[C:31]5[CH:35]=[CH:36][C:28]([O:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:20][C:16](=[O:19])[CH:17]=[CH2:18])=[CH:29][CH:30]=5)=[CH:9][CH:10]=4)[CH2:5][C:4]=3[CH:3]=2)=[O:33])=[CH:30][CH:29]=1)(=[O:19])[CH:17]=[CH2:18]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6344DichloromethaneHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidHCID 149383839H-Fluorene-2,7-diol

Product 1

HCID 226302692,7-Bis(4-(6-acryloyloxyhexyl)oxybenzoyloxy)fluoreneYield 22.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 2,7-dihydroxyfluorene (0.5 g), 4-(6-acryloyloxyhexyloxy)benzoic acid (1.62 g), EDC (1.06 g), DMAP (6.16 mg) and dichloromethane (30 mL) was stirred at a room temperature for 12 hours. Water was added to the reaction mixture to separate an organic layer, and the resulting organic layer was washed with water and dried on anhydrous magnesium sulfate. The solvent was distilled off from this organic layer under reduced pressure, and the resulting residue was purified by means of column chromatography (silica gel, eluting solvent: toluene/ethyl acetate [95/5]) and recrystallization (ethanol/ethyl acetate/toluene) to obtain 2,7-bis(4-(6-acryloyloxyhexyl)oxybenzoyloxy)fluorene (0.42 g) of colorless crystal.

Workup

  1. customto separate an organic layer
  2. washthe resulting organic layer was washed with water
  3. dry with materialdried on anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off from this organic layer under reduced pressure
  5. customthe resulting residue was purified by means of column chromatography (silica gel, eluting solvent: toluene/ethyl acetate [95/5]) and recrystallization (ethanol/ethyl acetate/toluene)

Sources & evidence

ORD record
ord-e0618c384d974f898d908e9202f951e7
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

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