Pyridine → 12-[(2-Methylprop-2-enoyl)oxy]dodecanoic acid
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].N1C=CC=CC=1.[C:22](Cl)(=[O:26])[C:23]([CH3:25])=[CH2:24]>O1CCCC1>[C:22]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])(=[O:26])[C:23]([CH3:25])=[CH2:24]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2.16 g of 12-hydroxydodecanoic acid in 30 ml of tetrahydrofuran (THF) is added 1.09 g of pyridine. The mixture is cooled to 0° C. and a solution of 1.04 g of methacryloyl chloride in 15 ml of THF is added dropwise. The mixture is allowed to warm to room temperature while stirring an is then stirred at ambient temperature for 12 hours. The solvent is then removed under reduced pressure and the residual solid is dissolved in 25 ml of diethylether. The solution is washed with distilled water, dried over magnesium sulfate and then evaporated to dryness. The product is purified by chromatography, using a 1:2 mixture of ethylacetate and hexane to give 1.5 g (53% yield) of 12-methacryloyloxydodecanoic acid.
Workup
- temperatureto warm to room temperature
- stirringan is then stirred at ambient temperature for 12 hours
- customThe solvent is then removed under reduced pressure
- dissolutionthe residual solid is dissolved in 25 ml of diethylether
- washThe solution is washed with distilled water
- dry with materialdried over magnesium sulfate
- customevaporated to dryness
- customThe product is purified by chromatography
- additiona 1:2 mixture of ethylacetate and hexane
Sources & evidence
- ORD record
- ord-32ef71bd624243a5a1bc252c460c5c2c
- Source dataset
- uspto-grants-1984_11
- Patent number
- US04485045
Reaction notes
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