Dimethylacetamide → Z-13-hexadecen-11-yn-1-yl acetate

HRID 1773123Notes

Reaction equation

HRID 1773123 reaction equation
[CH2:1](Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12]/[CH:13]=[CH:14]\[CH2:15][CH3:16].[C:18]([O-:21])(=[O:20])[CH3:19].[Na+].CN(C)C(=O)C>[I-].[Na+].O>[C:18]([O:21][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12]/[CH:13]=[CH:14]\[CH2:15][CH3:16])(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 31374DimethylacetamideHCID 517045Sodium AcetateHCID 117640717HCID 117640717, compound

Product 1

HCID 13072122Z-13-hexadecen-11-yn-1-yl acetateYield 94%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
122.5 °C

Procedure

In a reactor equipped with a stirrer, a cooling condenser, a dropping funnel and a thermometer were placed Z-13-hexadecen-11-yn-yl chloride (254.8 g:1.0 mol), sodium acetate (98.4 g:1.2 mol), sodium iodide (8.9 g:0.06 mol) and N,N-dimethylacetamide (113.2 g), and stirred at from 120 to 125° C. for 6 hours. After the completion of the reaction was confirmed by gas chromatography, water (350.0 g) was added to the reaction mixture. The organic phase separated from the aqueous phase was washed with an aqueous 1.0% by weight sodium bicarbonate solution (250.0 g). The organic phase was subjected to removal of the solvent under reduced pressure, followed by dehydration. The residue was then distilled under reduced pressure to obtain Z-13-hexadecen-11-yn-yl acetate [bp: from 126 to 130° C./0.13 KPa, 261.2 g, 0.94 mol]. [Yield: 93.8%]

Workup

  1. customIn a reactor equipped with a stirrer, a cooling condenser, a dropping funnel
  2. additionwas added to the reaction mixture
  3. customThe organic phase separated from the aqueous phase
  4. washwas washed with an aqueous 1.0% by weight sodium bicarbonate solution (250.0 g)
  5. customThe organic phase was subjected to removal of the solvent under reduced pressure
  6. distillationThe residue was then distilled under reduced pressure

Sources & evidence

ORD record
ord-716f8acf860247b8a85cf1de108ff300
Source dataset
uspto-grants-2016_02
Patent number
US09255056B2

Reaction notes

Loading…