Hydrochloric Acid → HCID 86645784, compound

HRID 573029Notes

Reaction equation

HRID 573029 reaction equation
[H-].[Na+].[CH2:3]([OH:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][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][CH3:24].[Br:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br.Cl>CCCCCC.C1(C)C=CC=CC=1>[CH2:3]([O:25][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][Br:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][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][CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12620Behenyl AlcoholHCID 187661,12-DibromododecaneHCID 24758Sodium hydride

Product 1

HCID 86645784HCID 86645784, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
85 °C

Procedure

Sodium hydride (60%, 0.98 g, 24.5 mmol) washed with hexane was suspended in toluene (16 ml), 1-docosanol (4.00 g, 12.2 mmol) was added, 1,12-dibromododecane (8.04 g, 24.5 mmol) was added, and the mixture was stirred at 85° C. for 2 days. The reaction mixture was cooled to room temperature, 1N hydrochloric acid (30 ml) was added dropwise thereto in a water bath to quench the reaction. The mixture was extracted with chloroform (100 ml), and washed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml), and once with 20% aqueous sodium chloride solution (30 ml). The organic layer was dried over sodium sulfate, and the solvent of the filtrate was evaporated. The residue was isolated and purified by silica gel column chromatography and precipitated with methanol (70 ml) to give 12-docosyloxy-dodecyl bromide (yield 78%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customin a water bath to quench
  3. customthe reaction
  4. extractionThe mixture was extracted with chloroform (100 ml)
  5. washwashed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent of the filtrate was evaporated
  8. customThe residue was isolated
  9. custompurified by silica gel column chromatography
  10. customprecipitated with methanol (70 ml)

Sources & evidence

ORD record
ord-dc0a9c05ed624003a7bdaffa1a49d96c
Source dataset
uspto-grants-2015_05
Patent number
US09029504B2

Reaction notes

Loading…