Pyridine → [6-(6-Isopentyloxyhexyloxy)-hexyl]-piperonyl ether

HRID 2398786Notes

Reaction equation

HRID 2398786 reaction equation
[CH2:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:2][CH:3]([CH3:5])[CH3:4].[CH2:21](Br)[C:22]1[CH:30]=[CH:29][C:28]2[O:27][CH2:26][O:25][C:24]=2[CH:23]=1.C(=O)(O)[O-].[Na+].N1C=CC=CC=1>CCOCC>[CH2:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][C:22]1[CH:30]=[CH:29][C:28]2[O:27][CH2:26][O:25][C:24]=2[CH:23]=1)[CH2:2][CH:3]([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 64514231,3-Benzodioxole, 5-(bromomethyl)-HCID 214340396-(6-Isopentyloxyhexyloxy)-hexanol

Product 1

HCID 68121476[6-(6-Isopentyloxyhexyloxy)-hexyl]-piperonyl ether

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.88 g (0.010 mol) of 6-(6-Isopentyloxyhexyloxy)-hexanol are mixed with 2.15 g (0.010 mol) of piperonyl bromide and 1.26 g (0.015 mol) of sodium bicarbonate and the mixture is stirred at 80° for 18 hours and then at 120° C. for 6 hours. 1.0 cc of pyridine is added to the reaction mixture which is heated to 80° over the course of 2 hours. The reaction mixture is cooled, taken up in ether, washed with 2N sulphuric acid, water and saturated sodium chloride solution, dried over magnesium sulphate and evaporated. After chromatography of the residue on silica gel with hexane/acetone (98:2) and (96:4), [6-(6-Isopentyloxyhexyloxy)-hexyl]-piperonyl ether is obtained as a colourless oil.

Workup

  1. waitat 120° C. for 6 hours
  2. temperatureis heated to 80° over the course of 2 hours
  3. temperatureThe reaction mixture is cooled
  4. washwashed with 2N sulphuric acid, water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-c5eced5aaf984491a2b68f6633d0e405
Source dataset
uspto-grants-1977_05
Patent number
US04025641

Reaction notes

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