Piperonal → HCID 68843936, compound

HRID 2116927Notes

Reaction equation

HRID 2116927 reaction equation
C([C:3]([CH2:36][CH3:37])(P([O-])([O-])=O)[C:4]1C=[CH:15][C:14]2[C:13]3[C:8](=[CH:9]C(C(CC)(CC)P([O-])([O-])=O)=[CH:11][CH:12]=3)[C:7]([CH2:29][CH2:30][CH3:31])(CCC)[C:6]=2[CH:5]=1)C.C1OC2C=CC(C=O)=CC=2O1.[OH-].[K+]>C1COCC1.CS(C)=O.C(O)C>[CH:36]([C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[C:29](=[CH:30][CH:31]=[CH:9][CH:8]=3)[CH2:15][C:14]=2[C:13]=1[CH:12]=[CH2:11])=[CH2:37]

Participants

7

Reactant 3

HCID 8438PiperonalHCID 14797Potassium HydroxideHCID 23110274HCID 23110274, compound

Product 1

HCID 68843936HCID 68843936, compoundYield 178.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 2,7-bis(diethylphosphonatomethyl)-9,9-dipropylfluorene (4) (2.70 g, 5 mmol), 3,4-methylenedioxybenzaldehyde (7) (1.60 g, 11 mmol) and potassium hydroxide (0.85 g, 15 mmol) in THF (30 mL) and DMSO (1 mL) was heated at 70° C. for 7 hours. The suspension was diluted with Ethanol (50 mL) and the solvent removed under vacuum. The product was purified by refluxing in Methanol followed by filtration. After drying, (II-5) was obtained as a pale yellow powder (1.95 g, 72%). The UV/VIS spectrum of (II-5) in methyl ethyl ketone (MEK) has two maxima at 382 nm and at 401 nm with a molar extinction coefficient of 79099 Mol−1 cm−1 and 63911 Mol−1 cm−1 respectively. Under UV irradiation (II-5) shows a strong blue fluorescence. The 1H-NMR data in CDCl3 are summarized in table 3.

Workup

  1. customthe solvent removed under vacuum
  2. customThe product was purified
  3. temperatureby refluxing in Methanol
  4. filtrationfollowed by filtration
  5. customAfter drying

Sources & evidence

ORD record
ord-0d25027fb03c4910bdf09e2b4b824317
Source dataset
uspto-grants-2008_10
Patent number
US07439537B2

Reaction notes

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