Dichloromethane → HCID 19901499, compound

HRID 2372247Notes

Reaction equation

HRID 2372247 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].C(Cl)Cl.[C:15](Cl)(=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:24])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 198603-Chloro-4-hydroxybenzoic acidHCID 69819Nonanoyl chloride

Product 1

HCID 19901499HCID 19901499, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.0 g (1.1×10-2 mol) of 3-chloro-4-hydroxy benzoic acid in 40 ml of dried methylene chloride containing 3.0 g (9.2×10-3 mol) of pyridine was added dropwise 3.0 g (9.2×10-3 mol) of nonanoic acid chloride, which were stirred under reflux for 7 hours. After the completion of the reaction, the solution was washed with an aqueous solution of 1 normal hydrochloric acid and further with water and dried on anhydrous magnesium sulfate. After magnesium sulfate was filtered off, the resulting product was purified through a silica gel column chromatography using methylene chloride and ethanol at 9:1 (v/v) as a developing solution and then recrystallized with 5 ml of ethanol to obtain 750 mg (yield: 25%) of a white solid.

Workup

  1. temperatureunder reflux for 7 hours
  2. customAfter the completion of the reaction
  3. washthe solution was washed with an aqueous solution of 1 normal hydrochloric acid and further with water
  4. dry with materialdried on anhydrous magnesium sulfate
  5. filtrationAfter magnesium sulfate was filtered off
  6. customthe resulting product was purified through a silica gel column chromatography
  7. customrecrystallized with 5 ml of ethanol

Sources & evidence

ORD record
ord-191632986e874ffc98ac26c069ddb4ea
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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