Methanol → HCID 54066049, compound

HRID 1576999Notes

Reaction equation

HRID 1576999 reaction equation
[Na].Br[CH2:3][CH:4]=[C:5]([CH3:18])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:17])[CH2:10][CH2:11][C:12]([CH3:16])=[C:13]([CH3:15])[CH3:14].[CH3:19][OH:20]>>[CH3:19][O:20][CH2:3][CH:4]=[C:5]([CH3:18])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:17])[CH2:10][CH2:11][C:12]([CH3:16])=[C:13]([CH3:15])[CH3:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 54124836HCID 54124836, compound

Product 1

HCID 54066049HCID 54066049, compound

Procedure

To a solution containing 8.6 g. of sodium dissolved in 172 ml. of absolute methanol, then was added dropwise over a period of 30 minutes, 111 g. of 1-bromo-3,7,10,11-tetramethyl-2,6,10-dodecatriene. The reaction mixture was refluxed for 16 hours. After reflux, the reaction mixture was dried under vacuum and poured onto ice water. The resulting mixture was exhaustively extracted with petroleum ether (b.p. 40°-45°C.). The combined petroleum ether extracts were washed neutral with saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. By chromatography on Kieselgel with hexane/diethylether (95:5 parts by volume) and distillation, there was obtained 1-methoxy-3,7,10,11-tetramethyl-2,6,10-dodecatriene, b.p. 87°-88°C./0.02 mmHg; nD20 = 1.4826

Workup

  1. additionTo a solution containing 8.6 g
  2. temperatureThe reaction mixture was refluxed for 16 hours
  3. temperatureAfter reflux
  4. customthe reaction mixture was dried under vacuum
  5. additionpoured onto ice water
  6. extractionThe resulting mixture was exhaustively extracted with petroleum ether (b.p. 40°-45°C.)
  7. washThe combined petroleum ether extracts were washed neutral with saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. distillationBy chromatography on Kieselgel with hexane/diethylether (95:5 parts by volume) and distillation

Sources & evidence

ORD record
ord-4fce6affdbb8422c98ea204e8898df5b
Source dataset
uspto-grants-1976_09
Patent number
US03983243

Reaction notes

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