Diethylene Glycol → HCID 22935640, compound

HRID 2253259Notes

Reaction equation

HRID 2253259 reaction equation
O=[C:2]([C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([C:20](=O)[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][CH:15]=3)[CH2:10][C:9]=2[CH:8]=1)[CH2:3][CH2:4][CH2:5][CH3:6].O.NN.C(O)COCCO.[OH-].[K+]>O>[CH2:2]([C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][CH:15]=3)[CH2:10][C:9]=2[CH:8]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 122666612,7-di(1-oxopentyl)fluorene

Product 1

HCID 22935640HCID 22935640, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A Dean-Stark trap with reflux condenser was fitted to a 1 liter conical flask, and 2,7-di(1-oxopentyl)fluorene (30.4129 g, 91.0566 mmol), hydrazine monohydrate (44.2 ml) and diethylene glycol (400 ml) were introduced and heated at 130° C. After 2 hours, KOH (20.5628 g) was added and heated at 200° C. After 3 hours, the reaction liquid was returned to room temperature, water was added, and the organic layer was extracted twice with ether. The organic layer was washed with 1N-HCl, saturated sodium bicarbonate solution, water (twice) and a saturated salt solution, and dried using MgSO4. The solution obtained was filtered, and concentrated under reduced pressure to obtain a crude product (27.6591 g, yellow solid). The crude product was purified by silica gel chromatography (hexane) to obtain 2,7-di-n-pentylfluorene (26.2137 g, yellow solid).

Workup

  1. temperatureA Dean-Stark trap with reflux condenser
  2. customwas fitted to a 1 liter conical flask
  3. temperatureheated at 200° C
  4. waitAfter 3 hours
  5. customthe reaction liquid
  6. customwas returned to room temperature
  7. extractionthe organic layer was extracted twice with ether
  8. washThe organic layer was washed with 1N-HCl, saturated sodium bicarbonate solution, water (twice) and a saturated salt solution
  9. customdried
  10. customThe solution obtained
  11. filtrationwas filtered
  12. concentrationconcentrated under reduced pressure
  13. customto obtain a crude product (27.6591 g, yellow solid)
  14. customThe crude product was purified by silica gel chromatography (hexane)

Sources & evidence

ORD record
ord-8fd232ba084f48849846e045cc02529c
Source dataset
uspto-grants-2008_01
Patent number
US07323538B2

Reaction notes

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