Hydrochloric Acid → HCID 123603665, compound
Reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[OH:20][CH2:21][CH:22](CO)[OH:23].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:1][C:2]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:3][CH2:4][C:5]([O:7][CH2:8][CH:21]([CH2:22][OH:23])[OH:20])=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
1.0 g (3.7 mmol) of methyl 4,8,12-trimethyltridec-3-enoate was slowly added dropwise to a solution of 0.86 g (9.3 mmol) of glycerol and 0.62 g (4.4 mmol) of potassium carbonate in dry N,N-dimethylformamide (4 mL) at 100° C. After the reaction mixture was stirred at 100° C. for 18 hours, 1M hydrochloric acid was added. The resulting 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 287 mg of the title compound (24% yield) as a colorless viscous liquid.
Workup
- extractionThe resulting solution was extracted with ether
- washthe extract was washed with saturated sodium bicarbonate aqueous solution and saturated brine
- dry with materialsuccessively, and dried over anhydrous sodium sulfate
- filtrationAfter filtration
- concentrationthe filtrate was concentrated
- customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane mixture)
Sources & evidence
- ORD record
- ord-e8a6a6b5399c4958850c45bcfe4d8f90
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703922B2
Reaction notes
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