1-Bromohexadecane → HCID 101909164, compound

HRID 1698290Notes

Reaction equation

HRID 1698290 reaction equation
[CH2:1]([O:6][C:7]1[C@@H:12]([C@H:13]([CH2:15][OH:16])[OH:14])[O:11][C:9](=[O:10])[C:8]=1[OH:17])[CH:2]([CH2:4][OH:5])[OH:3].C(=O)([O-])O.[Na+].[CH2:23](Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>CS(C)=O>[CH2:1]([O:6][C:7]1[C@@H:12]([C@H:13]([CH2:15][OH:16])[OH:14])[O:11][C:9](=[O:10])[C:8]=1[O:17][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])[CH:2]([CH2:4][OH:5])[OH:3]

Participants

5

Reactant 3

HCID 82131-BromohexadecaneHCID 516892Sodium BicarbonateHCID 672677953-Glyceryl ascorbate

Product 1

HCID 101909164HCID 101909164, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under an argon atmosphere, 3-O-glyceryl ascorbic acid (5.10 g) obtained in Example 1 was stirred in DMSO (20 mL), and further, sodium hydrogen carbonate (1.71 g) was added and the mixture was stirred at room temperature for 30 minutes. Thereafter, hexadecyl bromide (9.42 g) was added and 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 13.6 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:20/3/0.4), and concentration was performed under reduced pressure to obtain 3-O-glyceryl-2-O-hexadecyl ascorbic acid (4.09 g).

Workup

  1. temperaturethe mixture was heated up to 100° C.
  2. stirringstirred for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThen, the extracted liquid was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure, and 13.6 g of the resultant residue
  6. washElution
  7. concentrationwas performed with chloroform/methanol/water(volume ratio:20/3/0.4), and concentration

Sources & evidence

ORD record
ord-7a4d528f20a54edda125c7cd1f93fd38
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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