Acetic Anhydride → HCID 54482468, compound

HRID 1414815Notes

Reaction equation

HRID 1414815 reaction equation
[CH3:1][C:2]([CH:6]=[CH:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:3][CH2:4]O.C(OC(=O)C)(=O)C.P(Br)(Br)[Br:21]>>[Br:21][CH2:4][CH:3]=[C:2]([CH3:1])[CH:6]=[CH:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 24614Phosphorus tribromideHCID 54104975HCID 54104975, compound

Product 1

HCID 54482468HCID 54482468, compound

Procedure

A solution of 1.5 g. of 3,7,7-trimethyl-2,4-octadien-1-ol in 15 ml. of acetyl ether is added dropwise at -20° C. to 1.20 g. of phosphorus tribromide. The temperature is allowed to rise to 0° C. in the course of 30 minutes and then the mixture poured onto 30 ml. of ice-water. The mixture is extracted three times with diethyl ether, the extracts washed with water, 10% by weight aqueous potassium bicarbonate solution and semi-saturated and saturated aqueous sodium chloride solution and then dried over sodium sulfate. After removal of the solvent under reduced pressure in the cold, there is obtained 1-bromo-3,7,7-trimethyl-2,4-octadiene which exhibits a spot in the thin-layer chromatogram [Rf = 0.63; hexane/ethyl acetate (4:1 parts by volume)]. This substance is used in the process without further purification.

Workup

  1. customto rise to 0° C. in the course of 30 minutes
  2. additionthe mixture poured onto 30 ml
  3. extractionThe mixture is extracted three times with diethyl ether
  4. washthe extracts washed with water, 10% by weight aqueous potassium bicarbonate solution
  5. dry with materialsemi-saturated and saturated aqueous sodium chloride solution and then dried over sodium sulfate
  6. customAfter removal of the solvent under reduced pressure in the cold, there

Sources & evidence

ORD record
ord-4ecdccf6c0054e1eb4a63d3d6fad1728
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

Loading…