Water → HCID 131731340, compound

HRID 2369278Notes

Reaction equation

HRID 2369278 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]([CH2:22][CH2:23][CH2:24][CH:25]([CH3:37])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:36])[CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[CH:15][CH2:16][CH2:17][C:18](OC)=[O:19].O>S(=O)(=O)(O)O>[CH3:13][C:14]([CH2:22][CH2:23][CH2:24][CH:25]([CH3:37])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:36])[CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[CH:15][CH2:16][CH2:17][C:18]([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:19]

Participants

5

Reactant 3

HCID 962WaterHCID 54269534HCID 54269534, compoundHCID 54670067L-Ascorbic Acid

Product 1

HCID 131731340HCID 131731340, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

0.50 g (2.8 mmol) of ascorbic acid was dissolved in concentrated sulfuric acid (14 mL). After addition of 1.0 g (2.8 mmol) of methyl 5,9,13,17-tetramethyloctadec-4-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 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 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-4e6e776f8b5948e0be57569f585402ac
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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