Formic Acid → HCID 75995668, compound

HRID 2369266Notes

Reaction equation

HRID 2369266 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].[OH:26][CH2:27][C:28](CO)([CH2:31][OH:32])[CH2:29][OH:30].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:28]([CH2:31][OH:32])([CH2:29][OH:30])[CH2:27][OH:26])=[O:7]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8285PentaerythritolHCID 11430Potassium CarbonateHCID 54269534HCID 54269534, compound

Product 1

HCID 75995668HCID 75995668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under reduced pressure of 60-70 mmHg and nitrogen gas stream, 250 g (0.71 mol) of methyl 5,9,13,17-tetramethyloctadec-4-enoate was slowly added dropwise at 78-83° C. to a solution of 157 g (1.15 mol) of pentaerythritol and 1.58 g (1.15 mmol) of potassium carbonate in dry N,N-dimethylformamide (700 mL). 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 resulting insoluble matter 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 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 resulting insoluble matter 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. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate mixture)

Sources & evidence

ORD record
ord-7601e494972747f3afc9c106aafb45a1
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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