1-Bromohexadecane → HCID 19764351, compound

HRID 248155Notes

Reaction equation

HRID 248155 reaction equation
[H-].[Na+].[CH2:3]=[C:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:5][CH:6]([CH2:9][OH:10])[CH2:7][OH:8].[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>CN(C)C=O>[CH2:42]([O:10][CH2:9][CH:6]([CH2:5][C:4](=[CH2:3])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:7][OH:8])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH3:27]

Participants

5

Reactant 3

HCID 82131-BromohexadecaneHCID 24758Sodium hydrideHCID 19764336HCID 19764336, compound

Product 1

HCID 19764351HCID 19764351, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 80 mg of 60% sodium hydride in 20 ml of N,N-dimethylformamide is stirred at room temperature. A 680 mg portion of 2-(2-methyleneoctadecyl)-1,3-propanediol and 0.61 ml of hexadecylbromide are added and the mixture warmed very slowly to 60°-70° C. The mixture is evaporated, dissolved in ether, and is washed with water and brine then flash chromatographed (5% ethyl acetate:petroleum ether), to give 550 mg of the desired compound as colorless crystals, mp. 37°-38° C.

Workup

  1. temperaturethe mixture warmed very slowly to 60°-70° C
  2. customThe mixture is evaporated
  3. dissolutiondissolved in ether
  4. washis washed with water and brine
  5. customflash chromatographed (5% ethyl acetate:petroleum ether)

Sources & evidence

ORD record
ord-f3ff693710f64137a7c41bb38db9da7f
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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