Water → 2,2-Ethylenedioxy-10-methyl-6-oxa-9-undecene

HRID 436868Notes

Reaction equation

HRID 436868 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:9])=[CH:5][CH2:6][CH2:7][OH:8].Br[CH2:11][CH2:12][CH2:13][C:14]1([O:19][CH2:18][CH2:17][O:16]1)[CH3:15].O>CN(C)C=O>[CH2:17]1[CH2:18][O:19][C:14]([CH2:13][CH2:12][CH2:11][O:8][CH2:7][CH2:6][CH:5]=[C:4]([CH3:9])[CH3:3])([CH3:15])[O:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1365824-Methylpent-3-en-1-olHCID 5600542-(3-Bromopropyl)-2-methyl-1,3-dioxolane

Product 1

HCID 867348312,2-Ethylenedioxy-10-methyl-6-oxa-9-undeceneYield 31.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14 g of sodium hydride in a 50% suspension in oil were added to a solution of 28 g of 4-methyl-3-pentenol [Julia et al, Bull. Soc. Chim., (1960), p. 1072] in 250 ml of dimethylformamide and after stirring the mixture for 1 hour, 66 g of 5-bromo-2,2-ethylenedioxy-pentane were added thereto while keeping the temperature below 35° C. The mixture was stirred at room temperature for 17 hours and the reaction mixture was then poured into water. The mixture was extracted with petroleum ether (b.p.= 40°-75° C.) and the organic phase was washed with water, dried over sodium sulfate and evaporated to dryness. The residue was rectified to obtain 20 g of 2,2-ethylenedioxy-10-methyl-6-oxa-9-undecene in the form of a colorless liquid with a boiling point of 75° C. at 0.05 mm Hg.

Workup

  1. customthe temperature below 35° C
  2. stirringThe mixture was stirred at room temperature for 17 hours
  3. extractionThe mixture was extracted with petroleum ether (b.p.= 40°-75° C.)
  4. washthe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-427df9528e7f424f8ab0de4cda260480
Source dataset
uspto-grants-1977_06
Patent number
US04028386

Reaction notes

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