Water → HCID 178455718, compound

HRID 1722199Notes

Reaction equation

HRID 1722199 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:18]=[C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([CH2:25][CH3:26])[CH2:21][CH2:20]2)[CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[F:9][C:10]1[CH:18]=[C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([CH2:25][CH3:26])[CH2:21][CH2:20]2)[CH:16]=[CH:15][C:11]=1[C:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:13]

Participants

6

Reactant 3

HCID 962WaterHCID 97324-FluorophenolHCID 178455717HCID 178455717, compound

Product 1

HCID 178455718HCID 178455718, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

4-Fluorophenol (5.6 g, 0.05 mol) was dissolved in pyridine (10 ml), followed by adding to the solution, a solution of 2-fluoro-4-(trans-4-ethylcyclohexyl)benzoyl chloride (13.4 g, 0.05 mol) dissolved in toluene (50 ml), with stirring, thereafter heating the reaction mixture at 60° C. for 3 hours, adding water (100 ml) to the reaction material, washing the separated toluene layer with 6N HCl, then with 2N NaOH aqueous solution and further with water, thereafter drying it with anhydrous sodium sulfate, distilling off toluene and recrystallizing the residual solids from ethyl acetate to obtain the objective 4-fluorophenyl 2-fluoro-4-(trans-4-ethylcyclohexyl)benzoate (12.2 g, yield 65%). This compound exhibited following phase transition points:

Workup

  1. additionby adding to the solution
  2. washwashing the separated toluene layer with 6N HCl
  3. dry with materialwith 2N NaOH aqueous solution and further with water, thereafter drying it with anhydrous sodium sulfate
  4. distillationdistilling off toluene
  5. customrecrystallizing the residual solids from ethyl acetate

Sources & evidence

ORD record
ord-ced1fa32ab1e48e29446ae5ccd675cf4
Source dataset
uspto-grants-1989_08
Patent number
US04855076

Reaction notes

Loading…