Sodium Methoxide → (2E,7R,11R)-1-Methoxy-3,7,11,15-tetramethyl-2-hexadecene

HRID 2254655Notes

Reaction equation

HRID 2254655 reaction equation
[CH2:1](Cl)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH2:7][C@@H:8]([CH2:10][CH2:11][CH2:12][C@@H:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])\[CH3:4].[CH3:22][O-:23].[Na+]>CO.C(OCC)(=O)C>[CH2:1]([O:23][CH3:22])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH2:7][C@@H:8]([CH2:10][CH2:11][CH2:12][C@@H:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])\[CH3:4]

Participants

5

Conditions

Temperature
60 °C

Procedure

10.0 g of phytyl chloride was dropped into a solution of 2.0 g of sodium methoxide dissolved in 70 ml of methanol. The resulting mixture was stirred for 4 hours at 60° C. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was dissolved in 30 ml of ethyl acetate, and the resulting solution was washed with water. The solution was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue thus obtained was subjected to distillation (b.p.: 148°-150° C., 1.5 mmHg) to obtain 9.4 g (yield: 95%) of oily methyl phytyl ether.

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue obtained
  4. washthe resulting solution was washed with water
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue thus obtained
  8. distillationwas subjected to distillation (b.p.: 148°-150° C., 1.5 mmHg)

Sources & evidence

ORD record
ord-5bc8f7b74a8643cf87b0c24864c3fcbe
Source dataset
uspto-grants-1993_08
Patent number
US05236950

Reaction notes

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