Hydrochloric Acid → 3-(Octadecyloxy)-2,2-bis[(octadecyloxy)methyl]-1-propanol

HRID 537605Notes

Reaction equation

HRID 537605 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].Br[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][CH2:26][CH2:27][CH3:28].[H-].[Na+].Cl>C(Cl)(Cl)Cl.CN(C=O)C>[CH2:11]([O:1][CH2:2][C:3]([CH2:8][O:9][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11])([CH2:6][O:7][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11])[CH2:4][OH:5])[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][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 82181-BromooctadecaneHCID 8285PentaerythritolHCID 24758Sodium hydride

Product 1

HCID 142519643-(Octadecyloxy)-2,2-bis[(octadecyloxy)methyl]-1-propanolYield 23%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To pentaerythritol (1.5 g, 11.0 mmol) were added DMF (100 ml), 1-bromooctadecane (11.4 g, 34.2 mmol) and sodium hydride (60 wt %, 1.54 g, 38.5 mmol), and the mixture was stirred at 100° C. for 22 hr. The reaction mixture was cooled to room temperature, chloroform (150 ml) was added, and 1N hydrochloric acid (150 ml) was added further dropwise. After stirring, the aqueous layer was removed, and the organic layer was further washed with 1N hydrochloric acid (100 ml) and water (100 ml). The organic layer was evaporated under reduced pressure, and the residue was precipitated with methanol (150 ml), and the obtained precipitate was washed with methanol (150 ml). The crude crystals were dried and purified by silica gel column chromatography (hexane:chloroform=1:1→hexane:ethyl acetate=10:1) to give 2,2,2-tris(octadecyloxymethyl)ethanol (2.21 g, 2.47 mmol, yield 23%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringAfter stirring
  3. customthe aqueous layer was removed
  4. washthe organic layer was further washed with 1N hydrochloric acid (100 ml) and water (100 ml)
  5. customThe organic layer was evaporated under reduced pressure
  6. customthe residue was precipitated with methanol (150 ml)
  7. washthe obtained precipitate was washed with methanol (150 ml)
  8. customThe crude crystals were dried
  9. custompurified by silica gel column chromatography (hexane:chloroform=1:1→hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-873cd3b6e9b24fce859ea054116c8edc
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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