Formic Acid → HCID 86672620, compound

HRID 2369267Notes

Reaction equation

HRID 2369267 reaction equation
[CH3:1][C:2]([CH2:10][CH2:11][CH2:12][CH:13]([CH3:25])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[CH2:26]([OH:33])[C@@H:27]([C@@H:29](CO)[OH:30])[OH:28].C(=O)([O-])[O-].[K+].[K+].C(O)=O>CN(C)C=O>[CH3:1][C:2]([CH2:10][CH2:11][CH2:12][CH:13]([CH3:25])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C@@H:26]([C@@H:27]([CH2:29][OH:30])[OH:28])[OH:33])=[O:7]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 11430Potassium CarbonateHCID 222285ErythritolHCID 54269534HCID 54269534, compound

Product 1

HCID 86672620HCID 86672620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under reduced pressure of 60-70 mmHg and nitrogen gas stream, 199 g (0.564 mol) of methyl 5,9,13,17-tetramethyloctadec-4-enoate was slowly added dropwise to a solution of 191 g (1.56 mol) of erythritol and 1.58 g (1.15 mmol) of potassium carbonate in dry N,N-dimethylformamide (700 mL) at 78-83° C. After the reaction mixture was stirred at the same temperature for 10 hours, formic acid was added at 75° C. to adjust the pH to 4. After the resulting solution was subjected to vacuum concentration, the residue was diluted with t-butylmethylether (1.5 L), and the insoluble matter generated was separated by filtration. The filtrate was washed with 10% sodium bicarbonate aqueous solution twice, and decolorized with activated carbon (8 g). After filtration, the filtrate was concentrated, and the residue was dissolved in ethanol, followed by filtration through cellulose powder. After the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate mixture) to obtain the title compound.

Workup

  1. concentrationAfter the resulting solution was subjected to vacuum concentration
  2. additionthe residue was diluted with t-butylmethylether (1.5 L)
  3. customthe insoluble matter generated was separated by filtration
  4. washThe filtrate was washed with 10% sodium bicarbonate aqueous solution twice
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. dissolutionthe residue was dissolved in ethanol
  8. filtrationfollowed by filtration through cellulose powder
  9. concentrationAfter the filtrate was concentrated
  10. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate mixture)

Sources & evidence

ORD record
ord-952732901c5345ddbb08882789236cf6
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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