Water → Ethyl 7-[2-(ethenyloxy)ethoxy]heptanoate

HRID 2224753Notes

Reaction equation

HRID 2224753 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][OH:6])=[CH2:2].[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].O>C1(C)C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:2]=[CH:1][O:3][CH2:4][CH2:5][O:6][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 12995Hydroxyethyl vinyl etherHCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 71363567Ethyl 7-[2-(ethenyloxy)ethoxy]heptanoateYield 50.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-Hydroxyethyl vinyl ether (0.42 mol) was added dropwise to a flask, in which sodium hydride (0.42 mol) had been dispersed in anhydrous toluene (60 ml), under a nitrogen atmosphere. After the drop addition, ethyl 7-bromoheptanoate (0.42 mol) was added dropwise. Thereafter, tetrabutylammonium iodide (2 g) was immediately added to stir the mixture at 100° C. for 3 hours. The reaction mixture was poured into water, and the resultant-organic layer was washed with water and then combined with an extract from ether. The combined layer was dried over anhydrous sodium sulfate. After the solvent was removed, the resultant residue was distilled under reduced pressure to obtain 52 g of CH2═CHOCH2CH2O(CH2)6COOC2H5 (yield: 50.7%).

Workup

  1. additionwas added dropwise
  2. washthe resultant-organic layer was washed with water
  3. extractionan extract from ether
  4. dry with materialThe combined layer was dried over anhydrous sodium sulfate
  5. customAfter the solvent was removed
  6. distillationthe resultant residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-d79d243212474b459d59160349ad0f34
Source dataset
uspto-grants-2008_05
Patent number
US07378480B2

Reaction notes

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