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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Butyl 4-hydroxybenzoate is an organic compound, has proven to be a highly successful antimicrobial preservative in cosmetics, also used in medication suspensions, and as a flavoring additive in food.
Synonyms: Butyl parahydroxybenzoate; Butyl 4-hydroxybenzoate; AC40357
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Batch number can be found on the product's label following the word 'Batch'.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 94-26-8 |
Formula : | C11H14O3 |
M.W : | 194.23 |
SMILES Code : | O=C(OCCCC)C1=CC=C(O)C=C1 |
Synonyms : |
Butyl parahydroxybenzoate; Butyl 4-hydroxybenzoate; AC40357
|
MDL No. : | MFCD00016478 |
InChI Key : | QFOHBWFCKVYLES-UHFFFAOYSA-N |
Pubchem ID : | 7184 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.3% | Reflux; Ionic liquid; | Add p-hydroxybenzoic acid (1 mol), alcohol (5 mol) and benzimidazole ionic liquid (0.5 mol) to the dry three-necked flask, slowly warm up, reflux the reaction, and monitor by TLC until the reaction is completed; the solvent is distilled off under reduced pressure, and the remainder is used Wash with ethyl acetate and filter with suction. The filter cake is benzimidazole ionic liquid, which can be reused; the filtrate is spin-dried to obtain 95.3% yield of benzyl paraben, mp68-69 . |
94% | With 732 type macroporous resin; at 70℃; for 3.08333h;Microwave irradiation; | In the three bottles of p-hydroxybenzoic acid, n-butanol and 732 macroporous resin, the molar ratio of p-hydroxybenzoic acid to n-butanol was 1: 3.5, 732 macroporous resin was added in an amount of 25% of the total mass of the reactants. Three mouth bottles on the left side of the mouth plug mouth plug, the right mouth of the mouth probe tube (built-in temperature probe), the middle of the mouth connected to the air through the top of the furnace connected to the outside, respectively, equipped with water separator. Mixed evenly, and then into the electromagnetic stirrer, placed in a microwave oven, stirring, stirring speed of 270r / min. Began to react, the reaction process in time to release the separation of water within the water separator. Wherein, the microwave radiation power of 215W, microwave radiation temperature of 70 C, microwave irradiation time of 35min; Mixed evenly, and then placed in the electromagnetic stirrer, placed in a microwave oven, start stirring, start the reaction, the reaction process in time to release the separation of water within the water separator; After 2.5h reaction, turn off the power, the reaction liquid into the clean three bottles and steam distillation of excess n-butanol, distilled liquid into a clean beaker, cooling crystallization, washed with 10% sodium carbonate solution to pH 7.0-8.0, suction filtration, rinse the filter cake with distilled water, dry, refined white solid products of p-hydroxybenzoate. The yield of butyl p-hydroxybenzoate was determined to be 94%. |
92.3% | With methanesulfonic acid; choline chloride;Reflux; | In the first step, 1 mol of choline chloride and 2 mol of methanesulfonic acid are added to the reaction vessel, and stirred at 80 C until fully dissolved to obtain a low eutectic solvent;In the second step, after cooling the reaction system to room temperature, 1 mol of p-hydroxybenzoic acid and 1.2 mol of n-butanol are added, the temperature is slowly raised, and the reaction is refluxed, and TLC is monitored until the end of the reaction;In the third step, the reaction solution is cooled to room temperature, and a solid is precipitated, which is filtered with suction, and the filter cake is washed with a small amount of water to obtain paraben ester, the yield is 92.3%, m.p. 68-69 C; the filtrate is recovered to obtain a eutectic solvent. |
84.9% | With acetyl chloride; at 60℃; for 48h; | 4-Hydroxyzenzoicacid (2.0 g, 14.5 mmol) and acetyl chloride (200 mul, 2.2 mmol)were dissolved in 1-butanol (39.8 ml), and the reaction mixture was stirred at60C. After 48 h, the reaction mixture was evaporated to dryness. Theresulting residue was purified by Wakogel C-200 (Phi 3.0 x 25.0 cm), eluted withhexane/ethyl acetate (8:2, v/v), and then recrystallized with hexane to yieldbutyl 4-hydroxybenzoate (1.47 g, 84.9%). 1H NMR (CD3OD,500 MHz) delta: 1.03 (3H, t, J = 7.4 Hz); 1.52 (2H, sext, J= 7.3 Hz); 1.77 (2H, quin, J = 6.3Hz); 4.30 (2H, t, J = 6.6 Hz); 6.86(2H, d, J = 8.8 Hz); 7.90 (2H, d, J = 8.7 Hz). 13C NMR (CD3OD,500 MHz) delta: 14.10, 20.33, 31.99, 65.49, 116.12, 116.14,116.15, 122.45, 132.68, 163.50, 168.29. ESI-HRMS [M-H]-: calcd. ForC11H13O4: 193.0865, found 209.0870. HPLC: rt9.9 min, 99.5% purity. |
With ammonium iron(III) sulfate dodecahydrate; for 4h;Reflux; | 2) In the presence of a stirrer, a three-necked flask equipped with a reflux condenser and a thermometer, adding a certain amount of p-hydroxybenzoic acid, n-butanol and the catalyst obtained in step (1), wherein the catalyst is used in an amount of 5.3% of the total mass of p-hydroxybenzoic acid and n-butanol, the mass ratio of n-butanol to p-hydroxybenzoic acid was 3.5: 1, heated to reflux, water diversion, reaction 4h. Ater completion of the reaction, the catalyst was separated and the butanol was recovered by steam distillation, the distillate was poured into distilled water, stir with 10% sodium carbonate solution adjusted to pH 7-8, standing, until the solid product all precipitated, filtered, washed, dried, crude product; esterification rate of up to 97.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.9% | With benzothiazole hydrogen sulfate; for 4h;Reflux; Green chemistry; | General procedure: In the first step, add an appropriate amount of methanol to the reaction vessel, [HBth]HSO4And p-hydroxybenzoic acid, raised to reflux temperature for about 4h, TLC monitoring until the end of the reaction;In the second step, the methanol remaining in the mixture is distilled off, washed with ethyl acetate, filtered (filter cake is benzothiazole ionic liquid), the filtrate is steamed, washed with water, filtered, and dried to obtain colorless crystals. methylparaben; yield 96.9%. |