Piperonyl alcohol → [4-(4-Isopentyloxy-butyloxy)-butyl]-piperonyl ether

HRID 2398783Notes

Reaction equation

HRID 2398783 reaction equation
[CH2:1]([OH:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26].[H-].[Na+].[Br-].[Na+]>COCCOC>[CH2:23]([O:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][CH2:14][CH2:13][O:11][CH2:1][C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1)[CH2:24][CH:25]([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 10322Piperonyl alcoholHCID 24758Sodium hydrideHCID 253881Sodium BromideHCID 214340441-Bromo-4-(4-isopentyloxy-butyloxy)-butane

Product 1

HCID 68121315[4-(4-Isopentyloxy-butyloxy)-butyl]-piperonyl ether

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1.23 g (0.0081 mol) of piperonyl alcohol and 2.50 g (0.0085 mol) of 1-bromo-4-(4-isopentyloxy-butyloxy)-butane in 30 cc of absolute 1,2-dimethoxy-ethane, there is carefully added under nitrogen and while stirring, over the course of 20 minutes, 0.34 g (0.0077 mol) of 55% sodium hydride dispersion in oil. The mixture is stirred at 60° for 20 hours and the resulting sodium bromide is subsequently suction filtered, washed with ether and the filtrate is evaporated. After chromatography of the residue on silica gel with hexane/ethyl acetate (97:3) to (9:1), the [4-(4-Isopentyloxy-butyloxy)-butyl]-piperonyl ether is obtained as a colourless oil.

Workup

  1. washwashed with ether
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-bfa6608dfaa5473992e63b26c5d843ac
Source dataset
uspto-grants-1977_05
Patent number
US04025641

Reaction notes

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