1-Bromohexadecane → HCID 131729664, compound

HRID 1698295Notes

Reaction equation

HRID 1698295 reaction equation
[CH2:1]([O:9][C:10]1[C@@:15]([CH2:20][CH:21]([CH2:23][OH:24])[OH:22])([C@H:16]([CH2:18][OH:19])[OH:17])[O:14][C:12](=[O:13])[C:11]=1[OH:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(=O)([O-])O.[Na+].[CH2:31](Br)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>CS(C)=O>[CH2:1]([O:9][C:10]1[C@@:15]([CH2:20][CH:21]([CH2:23][OH:24])[OH:22])([C@H:16]([CH2:18][OH:19])[OH:17])[O:14][C:12](=[O:13])[C:11]=1[O:25][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH3:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 82131-BromohexadecaneHCID 516892Sodium BicarbonateHCID 131729665HCID 131729665, compound

Product 1

HCID 131729664HCID 131729664, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere, 3-O-octylglyceryl ascorbic acid (5.17 g) obtained in Example 8 was stirred in DMSO (10 mL), and further, sodium hydrogen carbonate (1.20 g) and hexadecyl bromide (5.22 g) were added. The mixture was heated up to 100° C. and stirred for 3 hours, followed by extraction with ethyl acetate. Then, the extracted liquid was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and 9.06 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:50/310.3), and concentration was performed under reduced pressure to obtain 3-O-octylglyceryl-2-O-hexadecyl ascorbic acid (3.41 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThen, the extracted liquid was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure, and 9.06 g of the resultant residue
  4. washElution
  5. concentrationwas performed with chloroform/methanol/water(volume ratio:50/310.3), and concentration

Sources & evidence

ORD record
ord-350630d9e2584f32bf4e7821a98dd574
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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