Hydrochloric Acid → HCID 123693628, compound

HRID 2369286Notes

Reaction equation

HRID 2369286 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:24])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[OH:25][CH2:26][CH:27](CO)[OH:28].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:1][C:2]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:24])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:3][CH2:4][C:5]([O:7][CH2:8][CH:26]([CH2:27][OH:28])[OH:25])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 753GlycerolHCID 11430Potassium CarbonateHCID 86672626HCID 86672626, compound

Product 1

HCID 123693628HCID 123693628, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.0 g (3.0 mmol) of methyl 4,8,12,16-tetramethylheptadec-3-enoate was slowly added dropwise to a solution of 0.68 g (7.4 mmol) of glycerol and 0.61 g (4.4 mmol) of potassium carbonate in dry N,N-dimethylformamide (3.5 mL) at 100° C. After the reaction mixture was stirred at 100° C. for 18 hours, 1M hydrochloric acid was added. The reaction solution was extracted with ether, and the extract was washed with 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 (ethyl acetate/hexane mixture) to obtain 347 mg of the title compound (29% yield) as a yellow viscous product.

Workup

  1. extractionThe reaction solution was extracted with ether
  2. washthe extract was washed with 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 (ethyl acetate/hexane mixture)

Sources & evidence

ORD record
ord-86626528f01a4960b8357bb36857a67a
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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