Diethyl Ether → HCID 54246900, compound

HRID 1606679Notes

Reaction equation

HRID 1606679 reaction equation
[CH3:1][C:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:3][CH2:4][CH2:5]O.CCOCC.P(Br)(Br)[Br:18]>N1C=CC=CC=1>[Br:18][CH2:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 54501832HCID 54501832, compound

Product 1

HCID 54246900HCID 54246900, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3 g. of 4-methyl-3-nonen-1-ol in a mixture of 20 ml. of ether and 1.25 ml. of pyridine under nitrogen is cooled in an ice-salt bath and stirred while 2.7 ml. of phosphorus tribromide is added slowly. The ice bath is removed and the mixture is allowed to warm to room temperature, then is heated under reflux for about 2.5 hrs. The mixture is then cooled in an ice bath while 10 ml. of water is added slowly. The layers are separated and the ether layer is washed with water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried over sodium sulfate, and evaporated, giving a residue comprising 1-bromo-4-methyl-3-nonene.

Workup

  1. customThe ice bath is removed
  2. temperatureis heated
  3. temperatureunder reflux for about 2.5 hrs
  4. temperatureThe mixture is then cooled in an ice bath while 10 ml
  5. additionof water is added slowly
  6. customThe layers are separated
  7. washthe ether layer is washed with water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-91e8ff733eb7443a8e73e0dd0eab0a47
Source dataset
uspto-grants-1976_04
Patent number
US03953499

Reaction notes

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