Pyridine → HCID 54124836, compound

HRID 1576998Notes

Reaction equation

HRID 1576998 reaction equation
[CH3:1][C:2](O)([CH2:5][CH2:6][CH:7]=[C:8]([CH3:16])[CH2:9][CH2:10][C:11]([CH3:15])=[C:12]([CH3:14])[CH3:13])[CH:3]=[CH2:4].N1C=CC=CC=1.P(Br)(Br)[Br:25]>CCCCCC>[Br:25][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:16])[CH2:9][CH2:10][C:11]([CH3:15])=[C:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 53643785HCID 53643785, compound

Product 1

HCID 54124836HCID 54124836, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

To a solution containing 223.9 g. of 3,7,10,11-tetramethyl-1,6,10-dodecatrien-3-ol in 570 ml. of hexane and 22.2 ml. of pyridine there was added dropwise at -7°C. over a period of two hours, 112 g. of phosphorous tribromide in 125 ml. of hexane. The resulting mixture was stirred for 30 minutes. After this, the reaction mixture was poured onto ice water and the reaction mixture was allowed to stand under constant stirring for 30 minutes. After 30 minutes, the reaction mixture was diluted with 1,000 ml. of hexane and the water layer was separated and the hexane layer was washed with water, aqueous sodium bicarbonate and finally with water. After washing, the hexane solution was dried over sodium sulfate and evaporated. There resulted 1-bromo-3,7,10,11-tetramethyl-2,6,10-dodecatriene.

Workup

  1. additionTo a solution containing 223.9 g
  2. additionAfter this, the reaction mixture was poured onto ice water
  3. stirringunder constant stirring for 30 minutes
  4. waitAfter 30 minutes
  5. additionthe reaction mixture was diluted with 1,000 ml
  6. customof hexane and the water layer was separated
  7. washthe hexane layer was washed with water, aqueous sodium bicarbonate and finally with water
  8. washAfter washing
  9. dry with materialthe hexane solution was dried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-3a30763c4f8d418f9e72326d286743e9
Source dataset
uspto-grants-1976_09
Patent number
US03983243

Reaction notes

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