Sodium → HCID 53812327, compound

HRID 1576995Notes

Reaction equation

HRID 1576995 reaction equation
[Na].C([O:5][CH2:6][CH:7]=[C:8]([CH3:21])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:20])[CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([CH3:18])[CH3:17])(=O)C>CO>[CH3:21][C:8]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:20])[CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([CH3:18])[CH3:17])=[CH:7][CH2:6][OH:5]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 54134791HCID 54134791, compound

Product 1

HCID 53812327HCID 53812327, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution containing 2.3 g. of sodium in 100 ml. of absolute methanol, there were added 41.8 g. of 1-acetoxy-3,7,10,11-tetramethyl-2,6,10-dodecatriene. The reaction mixture was allowed to stand for 16 hours at room temperature under constant stirring. The reaction mixture was then evaporated under vacuum and poured onto a saturated aqueous sodium chloride solution. After this, the reaction mixture was exhaustively extracted with petroleum ether (b.p. 40°-45°). The combined petroleum ether extracts were dried over sodium sulfate and evaporated. Distillation produced 3,7,10,11-tetramethyl-2,6,10-dodecatrien-1-ol, b.p. 92-93°C./0.02 mmHg; nD20 = 1.4947.

Workup

  1. additionTo a solution containing 2.3 g
  2. customThe reaction mixture was then evaporated under vacuum
  3. additionpoured onto a saturated aqueous sodium chloride solution
  4. extractionAfter this, the reaction mixture was exhaustively extracted with petroleum ether (b.p. 40°-45°)
  5. dry with materialThe combined petroleum ether extracts were dried over sodium sulfate
  6. customevaporated
  7. distillationDistillation

Sources & evidence

ORD record
ord-65cbeb6a9da44ee9adced24904b60289
Source dataset
uspto-grants-1976_09
Patent number
US03983243

Reaction notes

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