Water → 2,7-Di[4-(4-allyloxybutyloxy)benzoyloxy]-9-methylfluorene

HRID 2211572Notes

Reaction equation

HRID 2211572 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)[CH:2]=[CH2:3].[OH:19][C:20]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][C:26]([OH:33])=[CH:27][CH:28]=3)[CH:23]([CH3:34])[C:22]=2[CH:21]=1.Cl.C(N=C=N[CH2:41][CH2:42][CH2:43]N(C)C)C.[OH2:47]>C(Cl)Cl.CN(C1C=CC=CN=1)C>[CH2:3]([O:47][CH2:13][CH2:12][CH2:11][CH2:10][O:9][C:41]1[CH:42]=[CH:43][C:6]([C:5]([O:19][C:20]2[CH:32]=[CH:31][C:30]3[C:29]4[C:24](=[CH:25][C:26]([O:33][C:14](=[O:15])[C:13]5[CH:17]=[CH:18][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][CH2:1][CH:2]=[CH2:3])=[CH:11][CH:12]=5)=[CH:27][CH:28]=4)[CH:23]([CH3:34])[C:22]=3[CH:21]=2)=[O:4])=[CH:7][CH:8]=1)[CH:2]=[CH2:1]

Participants

7

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219606264-(4-Allyloxybutyloxy)benzoic acidHCID 219606279-methyl-9H-fluorene-2,7-diol

Product 1

HCID 219606302,7-Di[4-(4-allyloxybutyloxy)benzoyloxy]-9-methylfluorene

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

4-(4-Allyloxybutyloxy)benzoic acid 1.34 g and 2,7-dihydroxy-9-methylfluorene 0.46 g were dissolved in 30 ml of methylene chloride and cooled down to 5° C., and 0.01 g of dimethylaminopyridine and 1.15 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added thereto, followed by stirring the solution at a room temperature for 12 hours. Water 50 ml was added to separate the solution, and the organic layer was dried on anhydrous magnesium sulfate. A residue obtained after distilling the solvent off was refined by means of silica gel chromatography and recrystallized from a mixed solvent of ethanol and ethyl acetate to obtain 0.6 g of 2,7-di[4-(4-allyloxybutyloxy)benzoyloxy]-9-methylfluorene. Phase transition temperature: C 107 N 222 I

Workup

  1. customto separate the solution
  2. dry with materialthe organic layer was dried on anhydrous magnesium sulfate
  3. customA residue obtained
  4. distillationafter distilling the solvent
  5. customrecrystallized from a mixed solvent of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-180ad0539e6e48ecb10c480509950b77
Source dataset
uspto-grants-2006_09
Patent number
US07101595B2

Reaction notes

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