Water → HCID 178448098, compound

HRID 1194638Notes

Reaction equation

HRID 1194638 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH2:16]([C@H:19]1[CH2:24][CH2:23][C@H:22]([C:25](Cl)=[O:26])[CH2:21][CH2:20]1)[CH2:17][CH3:18].O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:16]([C@H:19]1[CH2:24][CH2:23][C@H:22]([C:25]([O:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)=[CH:10][CH:11]=2)=[O:26])[CH2:21][CH2:20]1)[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 113677374-(3,4-Difluorophenyl)phenolHCID 178448094HCID 178448094, compound

Product 1

HCID 178448098HCID 178448098, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

3,4-Difluoro-4'-hydroxybiphenyl (2.0 g, 10 mmols) was dissolved in dried pyridine (5 cc), followed by adding to the solution, a solution obtained by dissolving trans-4-propylcyclohexanecarboxylic acid chloride (2 g, 11 mmols) in dry toluene (10 cc), heating the mixture at 60° C. for 3 hours with stirring, then adding the resulting material to water (100 cc), then washing the separated toluene layer with 6N hydrochloric acid, 2N aqueous solution of NaOH and further with water, distilling off toluene from the toluene layer, and recrystallizing the residual crystals from ethyl acetate (10 cc) to obtain the objective 3,4-difluoro-4'-biphenylyl trans-4-propylcyclohexanecarboxylate (2.5 g, 70%).

Workup

  1. additionby adding to the solution
  2. customa solution obtained
  3. washwashing the separated toluene layer with 6N hydrochloric acid, 2N aqueous solution of NaOH
  4. distillationfurther with water, distilling off toluene from the toluene layer
  5. customrecrystallizing the residual crystals from ethyl acetate (10 cc)

Sources & evidence

ORD record
ord-06d39788c1ff494891dfe5e1cc1c27de
Source dataset
uspto-grants-1989_03
Patent number
US04816179

Reaction notes

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