Hydrochloric Acid → HCID 22167614, compound

HRID 2245905Notes

Reaction equation

HRID 2245905 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[I-].[K+].[OH-].[K+].Cl[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(O)C>[OH:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 748286-Chloro-1-hexanolHCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 22167614HCID 22167614, compoundYield 56.5%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of 25.00 g (133 mmol) of 6-hydroxy-2-naphthoic acid, 2.21 g (13 mmol) of potassium iodide, 4.28 g (13 mmol) of tetrabutylammonium bromide, and 77 g of ethanol, was added dropwise 18.63 g (332 mmol) of potassium hydroxide dissolved in 38 g of water. The mixture was heated to 60° C., 19.07 g (146 mmol) of 6-chloro-1-hexanol was added dropwise here, and the solution was refluxed for 34 hours. After adding hydrochloric acid dropwise, the reaction mixture was chilled with ice-water, and the precipitate was collected by filtration. Water was added to the precipitate, and the mixture was stirred for 30 minutes and filtered to recover the precipitate, which was dried in an oven at 40° C. overnight. The dried product was recrystallized from THF to yield the desired product, 6-(6-hydroxy-hexa-1-yloxy)-2-naphthoic acid as white solid (21.63 g, Yield: 56.5%).

Workup

  1. temperaturethe solution was refluxed for 34 hours
  2. filtrationthe precipitate was collected by filtration
  3. additionWater was added to the precipitate
  4. filtrationfiltered
  5. customto recover the precipitate, which
  6. customwas dried in an oven at 40° C. overnight
  7. customThe dried product was recrystallized from THF

Sources & evidence

ORD record
ord-d7f5a13f95f04fdab757217cbc84bded
Source dataset
uspto-grants-2010_03
Patent number
US07683203B2

Reaction notes

Loading…