ChemicalBook CAS DataBase List 4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid synthesis

10synthesis methods

Product Name:4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid
CAS Number:83883-26-5
Molecular formula:C16H20O5
Molecular Weight:292.33

14.0 g (58.8 mmol) of 4-(6-hydroxyhexyloxy)benzoic acid, 36.0 g (500 mmol) of acrylic acid, 2.00 g (11.7 mmol) of p-toluenesulfonic acid as an acid catalyst, and 1.20 g (11.8 mmol) of the polymerization inhibitor hydroquinone was dissolved in benzene. The mixed solution was refluxed in a flask connected to a Dean-Stark trap for about 12 hours until the amount of stoichiometry of water produced through the reaction was removed. After completion of the reaction, the solvent was distilled under reduced pressure, and the residue was dissolved in 300 mL of ethyl acetate. The mixed solution was washed with distilled water until no acrylic acid was found. At this time, the pH of the distilled water was checked to determine the presence of acrylic acid. Magnesium sulfate was added to the organic solution layer to dry the water. After filtration, the solvent was distilled under reduced pressure and recrystallized from isopropyl alcohol to obtain 4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid as a white powdery solid.

83883-25-4
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814-68-6
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4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

83883-26-5
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$8.00/250mg

Yield:83883-26-5 100%

Reaction Conditions:

in ISOPROPYLAMIDE at 25 - 30; for 1.25 h;Product distribution / selectivity;

Steps:

E.3

Example 3 (E 3) ; synthesis of compound 1:; In a 250 ml chemical reactor are dissolved 23.89 G (0.10 mol) of 4- (6-hydroxyhexyloxy) benzoic acid (PURITY-100%, preparation e. g. literature mentioned in example 1) in 100 G of dimethyl- acetamide at ca. 20°C. To the dear, stirred solution are gradually added 10.26 g (0.11 mol) of acryloyl chloride (Aldrich 96%), keeping the reaction temperature below 35°C by external cooling. After the addition, which takes about 15 minutes, the reaction mixture is stirred for 1 hours at 30°C, when TLC analysis (Silicagel, Cyclohexane : ETHYLACETATE : Acetic acid = 50: 50: 2, parts b. volume, UV fluorescence indicator) indicates completion of the reaction. A nearly colourless suspension is formed. It is gradually precipitated into 400 ml of cold water using a high speed stirrer (1300 rpm). After finishing the addition, the suspension is stirred for ?hour and filtered. The filter residue is washed twice with warm (-40°C) water (400 ml), filtered and the residue dried in vacuo at 25°C. The thus obtained colourless, crystalline solid is dissolved in 93.40 G toluene at 70°C, 0.14 9 of di-tert. butyl-p-cresole (BHT, polymerisation inhibitor) added and the solution cooled slowly to 0°C. The crystalline precipitate is filtered off and dried in vacuum at 35°C to constant weight. 24.40 G (83.5% o. th. ) of colourless, crystalline 4- (6-ACRYLOYLOXYHEXYLOXY) benzoic acid = compound (1) are obtained.

References:

WO2005/30696,2005,A1 Location in patent:Page/Page column 11-12

83883-25-4
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79-10-7 Synthesis