Pyridine → 12-[(2-Methylprop-2-enoyl)oxy]dodecanoic acid

HRID 279774

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

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 and 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
stirringis 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-99b296fbf2e847c594dfe9451a369d03
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587055

Linked notes

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