Water → HCID 131731347, compound

HRID 2369307Notes

Reaction equation

HRID 2369307 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]([CH2:21][CH2:22][CH2:23][CH:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:15][CH2:16][C:17](OC)=[O:18].O>S(=O)(=O)(O)O>[CH3:13][C:14]([CH2:21][CH2:22][CH2:23][CH:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:15][CH2:16][C:17]([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:18]

Participants

5

Reactant 3

HCID 962WaterHCID 54670067L-Ascorbic AcidHCID 78408912HCID 78408912, compound

Product 1

HCID 131731347HCID 131731347, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

0.65 g (3.7 mmol) of ascorbic acid was dissolved in concentrated sulfuric acid (18 mL). After addition of 1.0 g (3.7 mmol) of methyl 4,8,12-trimethyltridec-3-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-c7586b1b19ba47b3b5d694a4182eab6c
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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