1-Bromododecane → HCID 85976847, compound

HRID 560954Notes

Reaction equation

HRID 560954 reaction equation
[H-].[Na+].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Br.[CH2:16]([OH:29])[CH2:17][CH2:18][CH2:19][C:20]#[C:21][C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28]>CN(C=O)C>[OH:29][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21][C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH3:3]

Participants

5

Reactant 3

HCID 89191-BromododecaneHCID 24758Sodium hydrideHCID 5608785,7-Dodecadiyne-1,12-diol

Product 1

HCID 85976847HCID 85976847, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a glass reaction vessel, a suspension of 120 milligrams of sodium hydride was prepared in 10 milliliters dry DMF and 972 milligrams of 5,7-dodecadiyn-1,12-diol (HO(CH2)4C≡C—C≡C(CH2)4OH), was added. After stirring for 5 minutes 1.31 grams of CH3(CH2)11Br was added and the resulting mixture was stirred for 15 hours. The mixture was then quenched by addition of saturated NH4Cl solution and diluted with 100 milliliters of diethyl ether. The organic layer was separated and washed 3 times with brine, dried over MgSO4, filtered and the solvent was removed to yield a yellow oil. The oil was purified over silica gel (25%-35% by volume of ethyl acetate in hexanes gradient) to yield 606 milligrams of HO(CH2)4C≡C—C≡C(CH2)4O(CH2)11CH3 as a white solid.

Workup

  1. customIn a glass reaction vessel
  2. additionwas added
  3. customThe mixture was then quenched by addition of saturated NH4Cl solution
  4. additiondiluted with 100 milliliters of diethyl ether
  5. customThe organic layer was separated
  6. washwashed 3 times with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent was removed
  10. customto yield a yellow oil
  11. customThe oil was purified over silica gel (25%-35% by volume of ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-6eb4c5cabf0642a9b3ba3230b136fdf8
Source dataset
uspto-grants-2011_11
Patent number
US08063164B2

Reaction notes

Loading…