1-Butanol → HCID 21466808, compound

HRID 1939119Notes

Reaction equation

HRID 1939119 reaction equation
[CH2:1]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[CH:15]=[CH:14]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[K+].C(O)CCC.[CH2:35](Br)[CH2:36][CH2:37][CH2:38][CH3:39]>O>[CH2:1]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:23][CH:22]=1)[CH:15]=[CH:14]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 80571-BromopentaneHCID 14797Potassium HydroxideHCID 135976857HCID 135976857, compound

Product 1

HCID 21466808HCID 21466808, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution 0.8 g of 6-decyl-2-(4-hydroxyphenyl)quinoline and 170 mg potassium hydroxide in i2 ml of butanol, 0.5 g of pentyl bromide was added, followed by heat refluxing for 4 hours. After the reaction, the reaction mixture was poured into water and subjected to extraction with toluene. The organic layer was washed with water, dried with anhydrous sodium sulfate and subjected to distilling-off of the solvent, followed by purification by silica gel column chromatography and recrystallization to obtain 0.8 g of 6-decyl-2-(4-pentyloxyphenyl)quinoline. This compound showed the following phase transition series.

Workup

  1. temperatureby heat
  2. temperaturerefluxing for 4 hours
  3. customAfter the reaction
  4. extractionsubjected to extraction with toluene
  5. washThe organic layer was washed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customfollowed by purification by silica gel column chromatography and recrystallization

Sources & evidence

ORD record
ord-dbc1e4ffd3624504aaa695558c0ca417
Source dataset
uspto-grants-1997_12
Patent number
US05695684

Reaction notes

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