Pyridine → HCID 54362487, compound

HRID 2352592Notes

Reaction equation

HRID 2352592 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][CH:10]([Cl:15])[CH:11]([CH3:14])[CH2:12][CH3:13])=[O:7])=[CH:4][CH:3]=1.N1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][CH:10]([Cl:15])[CH:11]([CH3:14])[CH2:12][CH3:13])=[O:7])=[CH:4][CH:3]=2)=[O:7])=[CH:16][CH:17]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:13][CH2:12][CH2:11][CH:10]=[CH2:9]

Participants

4

Reactant 2

HCID 1049PyridineHCID 13955492HCID 13955492, compound

Product 1

HCID 54362487HCID 54362487, compoundYield 149.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 0.82 g of p-(decenyloxy)benzoic acid prepared by the procedure of Example 4.(1) was added toluene and the mixture was cooled with ice. To the mixture was dropped 1.1 g of thionyl chloride, and reaction was carried out for 7 hours at 80° C. After the reaction, the resulting reaction solution was concentrated to obtain an acid chloride compound. 0.76 g of 2-chloro-3-methylpentyl p-hydroxybenzoate and 0.5 g of pyridine were dissolved in toluene, and the resulting solution was cooled with ice. To the solution was dropped a toluene solution of the above-obtained acid chloride compound. Reaction was carried out for 15 hours at rool temperature. After the reaction, the resulting reaction solution was washed with water and dried over magnesium sulfate, and the solvent was then distilled out under reduced pressure. The residue was purified by column chromatography to obtain 1.14 g of the objective ester compound. (Yield: 74%).

Workup

  1. temperaturethe resulting solution was cooled with ice
  2. customReaction
  3. customAfter the reaction
  4. customthe resulting reaction solution
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was then distilled out under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-489cb73598144ebba28526e0ee222a9e
Source dataset
uspto-grants-1989_10
Patent number
US04877858

Reaction notes

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