Potassium Carbonate → 4-(4-(Trifluoromethyl)phenoxy)benzaldehyde

HRID 2377720Notes

Reaction equation

HRID 2377720 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 680234-Fluorobenzaldehyde

Product 1

HCID 133008444-(4-(Trifluoromethyl)phenoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-(trifluoromethyl)phenol (4.86 g, 1 equiv), 4-fluorobenzaldehyde (3.22 mL, 1 equiv), potassium carbonate (4.15 g, 1 equiv) and dimethylformamide (60 mL) was stirred at 150° C. under argon for 3 hours, then poured into ice/water. The precipitate was filtered off, washed with water, then extracted with hot ethanol. Undisolved solid was removed by filitration, and the filtrate evaporated and purified by chromatography on silica. 1H-NMR (CDCl3) δ 7.14 (4H, m), 7.66 (2H, m), 7.90 (2H, m), 9.97 (1H, s); MS (APCI+). found (M+1)=267; C14H9F3O2, requires 266.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. extractionextracted with hot ethanol
  4. customwas removed by filitration
  5. customthe filtrate evaporated
  6. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-a0379af77efc4229b95e0e9b6b0fd61e
Source dataset
uspto-grants-2008_12
Patent number
US07470694B2

Reaction notes

Loading…