3,4-Difluorobenzoyl chloride → HCID 178444574, compound

HRID 2309669Notes

Reaction equation

HRID 2309669 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[F:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17](Cl)=[O:18]>N1C=CC=CC=1.C1(C)C=CC=CC=1.O>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([O:12][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:22]([F:23])=[C:14]([F:13])[CH:15]=2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 2

HCID 27245193,4-Difluorobenzoyl chlorideHCID 178444573HCID 178444573, compound

Product 1

HCID 178444574HCID 178444574, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of trans-4-pentylcyclohexanol (1.9 g 0.011 mol) dissolved in dry pyridine (5 ml) was added a solution of 3,4-difluorobenzoyl chloride (2.0 g, 0.011 mol) dissolved in dry toluene (10 ml), followed by heating the mixture at 60° C. for 3 hours, thereafter pouring the reaction mixture in water (100 ml), separating the toluene layer, washing it with 6N hydrochloric acid, then with 2N-NaOH aqueous solution and further with water, drying with anhydrous sodium sulfate, distilling off toluene from the resulting toluene solution and recrystallizing the remaining oily product from ethanol to obtain the objective 3,4-difluorobenzoic acid-trans-4-pentylcyclohexyl ester (2.4 g, 0.0077 mol) (yield: 70%). This product has a m.p. of 26.9° C., and its N-I point sought from a mixture thereof with trans-4-alkyl-(4-cyanophenyl)cyclohexanes according to extrapolation method was -6.0° C. Further its elemental analysis values were as follows: C: 70.03%, H: 7.81% (calculated values, C: 69.65% and H: 7.79%).

Workup

  1. customseparating the toluene layer
  2. washwashing it with 6N hydrochloric acid
  3. dry with materialwith 2N-NaOH aqueous solution and further with water, drying with anhydrous sodium sulfate
  4. distillationdistilling off toluene from the resulting toluene solution
  5. customrecrystallizing the remaining oily product from ethanol

Sources & evidence

ORD record
ord-baaa3c427b084013b72c2aed22a11d74
Source dataset
uspto-grants-1987_09
Patent number
US04696759

Reaction notes

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