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

HRID 1982750Notes

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

Conditions

Temperature: 5 °C

Procedure

1.34 g of 4-(4-allyloxybutyloxy)benzoic acid and 0.46 g of 2,7-dihydroxy-9-methylfluorene were dissolved in 30 ml of methylene chloride and cooled to 5° C. 0.01 g of dimethylaminopyridine and 1.15 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added to it, and stirred at room temperature for 12 hours. 50 ml of water was added to it for liquid-liquid separation, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was purified through 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.

Workup

dry with materialthe organic layer was dried with anhydrous magnesium sulfate
customThe solvent was evaporated away
customthe resulting residue was purified through silica gel chromatography
customrecrystallized from a mixed solvent of ethanol and ethyl acetate

Sources & evidence

ORD record: ord-5dc462272ead4de2b68e92f2bb2fb02d
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541071B2

Reaction notes

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