1-Iodooctane → 2-(4-Decyloxyphenyl)-5-octyloxybenzoxazole

HRID 1108931Notes

Reaction equation

HRID 1108931 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:21]=3[N:22]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[K+].[CH2:30](I)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(O)CCC>[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]3[CH:26]=[CH:25][C:24]([O:27][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:23][C:21]=3[N:22]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 123801-IodooctaneHCID 14797Potassium HydroxideHCID 190211502-(4-Decyloxyphenyl)-5-hydroxybenzoxazole

Product 1

HCID 190211452-(4-Decyloxyphenyl)-5-octyloxybenzoxazoleYield 52.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In a 20 ml-round-bottomed flask, 0.25 g (0.68 mM) of 2-(4-decyloxyphenyl)-5-hydroxybenzoxazole, 0.08 g (1.21 mM) of potassium hydroxide and 3 ml of butanol were placed and heated to provide a solution. To the solution, 0.18 ml (1.00 mM) of octyl iodide was added, followed by heat-refluxing for 5 hours and 40 minutes under stirring. After the reaction, the solvent in the reaction mixture was distilled off under reduced pressure. To the residue, ethyl acetate and water were added, followed by stirring at room temperature. The organic layer was successively washed with 2%-sodium thiosulfate aqueous solution and water, followed by drying with anhydrous sodium sulfate and reduced pressure distillation. The resultant residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (acetone-methanol) to obtain 0.17 g of 2-(4-decyloxyphenyl)-5-octyloxybenzoxazole (Yield: 52.1%). ##STR82##

Workup

  1. temperatureheated
  2. customto provide a solution
  3. temperatureby heat-refluxing for 5 hours and 40 minutes
  4. customAfter the reaction
  5. distillationthe solvent in the reaction mixture was distilled off under reduced pressure
  6. additionTo the residue, ethyl acetate and water were added
  7. stirringby stirring at room temperature
  8. washThe organic layer was successively washed with 2%-sodium thiosulfate aqueous solution and water
  9. dry with materialby drying with anhydrous sodium sulfate and reduced pressure distillation
  10. customThe resultant residue was purified by silica gel column chromatography (eluent: toluene)
  11. customrecrystallized from a mixture solvent (acetone-methanol)

Sources & evidence

ORD record
ord-3740d790ac7e4227bbce872df542252e
Source dataset
uspto-grants-1994_06
Patent number
US05318720

Reaction notes

Loading…