Water → 4'-Propyl-bicyclohexyl-4-carboxylic acid 3-acryloyloxy-propyl ester

HRID 386327

Reaction equation

[C:1]([O-:5])(=[O:4])[CH:2]=[CH2:3].[Na+].CC(=C)C(OCCC[CH2:15][CH2:16][CH2:17][O:18][C:19]([CH:21]1[CH2:26][CH2:25][CH:24]([CH:27]2[CH2:32][CH2:31][CH:30]([CH2:33][CH2:34][CH2:35]CC)[CH2:29][CH2:28]2)[CH2:23][CH2:22]1)=[O:20])=O.[I-].[Na+].O>CN(C)C=O>[C:1]([O:5][CH2:15][CH2:16][CH2:17][O:18][C:19]([CH:21]1[CH2:26][CH2:25][CH:24]([CH:27]2[CH2:28][CH2:29][CH:30]([CH2:33][CH2:34][CH3:35])[CH2:31][CH2:32]2)[CH2:23][CH2:22]1)=[O:20])(=[O:4])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of sodium acrylate (2.5 g, 13.4 mmol), 4′-propyl-bicyclohexyl-4-carboxylic acid 3-bromo-propyl ester (synthesis described for preferred example 1) (5.0 g, 13.4 mmol) and sodium iodide (2.5 g, 16.7 mmol) in dimethylformamide (150 ml) is stirred at 130° C. overnight. The mixture is cooled to room temperature, poured into water, and this is extracted twice with diethyl ether. The ethereal solution is washed with water and then dried over sodium sulphate. The solution is evaporated to dryness and purified by flash column chromatography using DCM/petrol (1/1) as eluant to give upon evaporation of the appropriate fractions a colourless oil.

Workup

temperatureThe mixture is cooled to room temperature
extractionthis is extracted twice with diethyl ether
washThe ethereal solution is washed with water
dry with materialdried over sodium sulphate
customThe solution is evaporated to dryness
custompurified by flash column chromatography
customto give upon evaporation of the appropriate fractions a colourless oil

Sources & evidence

ORD record: ord-3352ca3e5f3a43e796f555dd60c1a09a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372307B2

Linked notes

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