Water → 4-[3-(Perfluorooctyl)-1-propyloxy]benzaldehyde

HRID 2104306Notes

Reaction equation

HRID 2104306 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1C=O.[F:16][C:17]([F:44])([CH2:40][CH2:41][CH2:42]I)[C:18]([F:39])([F:38])[C:19]([F:37])([F:36])[C:20]([F:35])([F:34])[C:21]([F:33])([F:32])[C:22]([F:31])([F:30])[C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25].O>CN(C=O)C.CCOCC>[F:16][C:17]([F:44])([CH2:40][CH2:41][CH2:42][O:7][C:8]1[CH:9]=[CH:12][C:13]([CH:1]=[O:4])=[CH:14][CH:15]=1)[C:18]([F:38])([F:39])[C:19]([F:36])([F:37])[C:20]([F:34])([F:35])[C:21]([F:32])([F:33])[C:22]([F:31])([F:30])[C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25]

Participants

7

Reactant 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 111575823-(Perfluorooctyl)propyl iodide

Product 1

HCID 121541694-[3-(Perfluorooctyl)-1-propyloxy]benzaldehydeYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A 500 mL 2-neck flask equipped with thermometer and gas inlet charged with potassium carbonate (27.6 g), hydroxy benzaldehyde (13.4 g), and 3-(perfluorooctyl)propyl iodide (58.8 g) in DMF (200 mL) was heated to 65° C. (internal temperature). The mixture was stirred at 65° C. until the reaction was complete. The reaction mixture was cooled to room temperature. Water (300 mL) and ether (300 mL) were added and the mixture stirred vigorously for 5 min. The layers were separated and the organic layer retained. The aqueous layer was extracted with ether (3×200 mL). The combined organic layers were washed with water (2×100 mL), Na2S2O3 (1×100 mL), 2.5 N NaOH (3×100 mL), and aqueous NaCl (1×100 mL). The organic layer was dried over MgSO4, filtered and concentrated. The product was further dried under high vacuum for 5 h to give desired product (53 g, 91% yield). The structure of the product was characterized 1H NMR.

Workup

  1. customA 500 mL 2-neck flask equipped with thermometer and gas inlet
  2. temperatureThe reaction mixture was cooled to room temperature
  3. stirringthe mixture stirred vigorously for 5 min
  4. customThe layers were separated
  5. extractionThe aqueous layer was extracted with ether (3×200 mL)
  6. washThe combined organic layers were washed with water (2×100 mL), Na2S2O3 (1×100 mL), 2.5 N NaOH (3×100 mL), and aqueous NaCl (1×100 mL)
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was further dried under high vacuum for 5 h

Sources & evidence

ORD record
ord-defe4046821d4c0aa6626f66ab256746
Source dataset
uspto-grants-2009_08
Patent number
US07576245B2

Reaction notes

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