Diethyl Ether → HCID 21273105, compound

HRID 1382703Notes

Reaction equation

HRID 1382703 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].CCOCC>C1C=CC=CC=1>[CH2:5]([C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][Br:2])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 53828330HCID 53828330, compound

Product 1

HCID 21273105HCID 21273105, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 10 g of phosphorus tribromide in 50 ml of benzene is added dropwise over a period of 15 minutes to a stirred mixture of 6.6 g of 2-nonylbenzyl alcohol and 50 ml of benzene. The reaction mixture is heated under reflux for 30 minutes and, after cooling, ice-water and ether are added. The organic phase is separated off, washed with water, dried over sodium sulphate and concentrated by evaporation in vacuo. Chromatographic purification of the residue on silica gel with petroleum ether yields 2-nonylbenzyl bromide in the form of a colourless oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureafter cooling
  4. customThe organic phase is separated off
  5. washwashed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation in vacuo
  8. customChromatographic purification of the residue on silica gel with petroleum ether

Sources & evidence

ORD record
ord-bc73581ef9834b3288ecdbf6085cd5b6
Source dataset
uspto-grants-1989_02
Patent number
US04808572

Reaction notes

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