1,2-Dichloroethane → 2,7-Bis(4-(6-acryloyloxyhexyl)oxybenzoyloxy)-9-methylfluorene

HRID 2416366Notes

Reaction equation

HRID 2416366 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)[CH:5]([CH3:16])[C:4]=2[CH:3]=1.[C:17]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1)(=[O:20])[CH:18]=[CH2:19].[CH2:38](Cl)[CH2:39]Cl.ClCCl>CN(C1C=CN=CC=1)C.O>[C:17]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:39]1[CH:38]=[CH:36][C:32]([C:33]([O:1][C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([O:15][C:33](=[O:34])[C:32]5[CH:36]=[CH:37][C:29]([O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:17](=[O:20])[CH:18]=[CH2:19])=[CH:30][CH:31]=5)=[CH:9][CH:10]=4)[CH:5]([CH3:16])[C:4]=3[CH:3]=2)=[O:34])=[CH:31][CH:30]=1)(=[O:20])[CH:18]=[CH2:19]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6344DichloromethaneHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidHCID 219606279-methyl-9H-fluorene-2,7-diol

Product 1

HCID 220350072,7-Bis(4-(6-acryloyloxyhexyl)oxybenzoyloxy)-9-methylfluoreneYield 10.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 2,7-dihydroxy-9-methylfluorene (0.5 g), 4-(6-acryloyloxyhexyloxy)benzoic acid (1.52 g), EDC (0.99 g), DMAP (5.76 mg) and dichloromethane (30 mL) was stirred at a room temperature for 12 hours. Water was added to the reaction mixture, and the separated 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) to obtain 2,7-bis(4-(6-acryloyloxyhexyl)oxybenzoyloxy)-9-methylfluorene (0.19 g) of a white solid matter.

Workup

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

Sources & evidence

ORD record
ord-9c38f7096ab2404f90550eb351a0b975
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

Loading…