Water → HCID 13668411, compound

HRID 247355Notes

Reaction equation

HRID 247355 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH2:11]([O:13][CH2:14][CH2:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)[CH3:12].O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:11]([O:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([O:10][C:4]2[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([F:1])[CH:3]=2)=[O:22])=[CH:24][CH:25]=1)[CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 136684104-(2-Ethoxyethoxy)benzoyl chloride

Product 1

HCID 13668411HCID 13668411, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-fluoro-4-cyanophenol (1.5 g, 11 mmols) dissolved in dry pyridine (5 cc) was added a solution of 4-(β-ethoxyethoxy)benzoic acid chloride (2.5 g, 11 mmols) dissolved in dry toluene (10 cc), followed by heating the mixture with stirring at 60° C. for 3 hours, thereafter adding it to water (100 cc), washing the resulting separated toluene layer with 6N-hydrochloric acid, 2N-NaOH aqueous solution and water, in this order, drying over anhydrous sodium sulfate, distilling off toluene from the toluene layer and recrystallizing the resulting oily residue from ethyl alcohol (10 cc) to obtain the objective 3-fluoro-4-cyanophenyl 4-(β-ethoxyethoxy)benzoate (2.1 g) (yield: 64%).

Workup

  1. temperatureby heating the mixture
  2. washwashing the resulting
  3. customseparated toluene layer with 6N-hydrochloric acid, 2N-NaOH aqueous solution and water
  4. dry with materialin this order, drying over anhydrous sodium sulfate
  5. distillationdistilling off toluene from the toluene layer
  6. customrecrystallizing the resulting oily residue from ethyl alcohol (10 cc)

Sources & evidence

ORD record
ord-f179a9681a474257ad1a326846788485
Source dataset
uspto-grants-1987_11
Patent number
US04707296

Reaction notes

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