Pyridine → HCID 19792972, compound

HRID 6320Notes

Reaction equation

HRID 6320 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([O:8][CH2:9][CH:10]([F:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:7])=[CH:4][CH:3]=1.N1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[CH2:21]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:1][C:2]2[CH:19]=[CH:18][C:5]([C:6]([O:8][CH2:9][CH:10]([F:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:7])=[CH:4][CH:3]=2)=[O:7])=[CH:18][CH:19]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:13][CH2:12][CH2:11][CH:10]=[CH2:9]

Participants

4

Reactant 2

HCID 1049PyridineHCID 14401550HCID 14401550, compound

Product 1

HCID 19792972HCID 19792972, compoundYield 167.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 3.0 g of 4-(9-decenyloxy)benzoic acid prepared in the same manner as in 9.(2) in Example 9 added was toluene, and the mixture was cooled in an ice bath. 2.0 g of thionyl chloride was added dropwise to the mixture. Subsequently, reaction was carried out for 3 hours at 80° C. After conclusion of the reaction, the product was concentrated to obtain an acid chloride compound. While, 1.7 g of 2-fluorooctyl 4-hydroxybenzoate and 0.9 g of pyridine were dissolved in toluene, and the resulting solution was cooled in an ice bath. Added dropwise thereto was a toluene solution of the above-described acid chloride compound. Reaction was then carried out for 15 hours at room temperature. After conclusion of the reaction, the product was washed with water and dried over magnesium sulfate, and the solvent was then distilled out from the dried product under reduced pressure. The residue was purified by column chromatography to obtain 2.8 g of the objective ester compound. (Yield: 85%)

Workup

  1. temperaturethe resulting solution was cooled in an ice bath
  2. additionAdded dropwise
  3. customReaction
  4. customAfter conclusion of the reaction
  5. washthe product was washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was then distilled out from the dried product under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9b9269591a114f26bc8d123006fad2bc
Source dataset
uspto-grants-1993_09
Patent number
US05248446

Reaction notes

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