Water → mono-O-(3,7,11,15-tetramethylhexadec-2-enoyl)ascorbic acid

HRID 2369294Notes

Reaction equation

HRID 2369294 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].[CH3:13][C:14]([CH2:20][CH2:21][CH2:22][CH:23]([CH3:35])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:34])[CH2:28][CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[CH:15][C:16](OC)=[O:17].O>S(=O)(=O)(O)O>[CH3:13][C:14]([CH2:20][CH2:21][CH2:22][CH:23]([CH3:35])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:34])[CH2:28][CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[CH:15][C:16]([O:4][C:3]1[C:2]([O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]=1[OH:6])=[O:1])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 54670067L-Ascorbic AcidHCID 85914815CID 85914815

Product 1

HCID 131731343mono-O-(3,7,11,15-tetramethylhexadec-2-enoyl)ascorbic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

0.55 g (3.1 mmol) of ascorbic acid was dissolved in concentrated sulfuric acid (14 mL). After addition of 1.0 g (3.1 mmol) of methyl 3,7,11,15-tetramethylhexadec-2-enoate, the mixture was stirred for 24 hours at room temperature. The reaction mixture was poured into iced water, and extracted with ethyl acetate. The extract was washed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine, successively, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (methanol/methylene chloride mixture) to obtain the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine
  3. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe resulting residue was purified by silica gel column chromatography (methanol/methylene chloride mixture)

Sources & evidence

ORD record
ord-58f20d390f6045f2accca54309f73062
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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