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Product Details of Methyl 3,3-dimethoxypropionate

CAS No. :7424-91-1
Formula : C6H12O4
M.W : 148.16
SMILES Code : O=C(OC)CC(OC)OC
MDL No. :MFCD00010650
InChI Key :SMCVPMKCDDNUCQ-UHFFFAOYSA-N
Pubchem ID :81924

Safety of Methyl 3,3-dimethoxypropionate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Methyl 3,3-dimethoxypropionate

* 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.

  • Downstream synthetic route of [ 7424-91-1 ]

[ 7424-91-1 ] Synthesis Path-Downstream   1~10

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YieldReaction ConditionsOperation in experiment
To a dry 250ml 3-necked flask, sodium hydride (60percent in oil) (778mg, 32.4mmol) was added in diethyl ether (35ml). A condenser was attached and the flask placed under an atmosphere of argon. The mixture was stirred and cooled to 0 0C. Ethyl formate (22ml, 270mmol) was added dropwise, followed by a solution of methyl 3,3- bis(methyloxy)propanoate (3.83ml, 27.0mmol) in diethyl ether (25ml) added dropwise over 10 minutes. The mixture was stirred at 0 0C for 1.5 hours and then warmed to room temperature overnight. Poured into 100ml of ice-water and extracted with diethyl ether (3 x 50 ml) which was discarded. The aqueous phase was acidified (pH 3) with concentrated HCI (3ml) and extracted with dichloromethane (5 x 50ml), dried, filtered and evaporated. The residue was purified using silica gel chromatography, eluting with a mixture of methanol and dichloromethane (0-25percent) to afford the product (D32); MS (ES+) m/e 143 [M-H]".
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YieldReaction ConditionsOperation in experiment
Montmorillonite K10; at 0℃;Product distribution / selectivity; Example 1: Preparation of methyl 3,3-dimethoxypropionate Simultaneously, but separately, 150 kg/h (1.413 kmol/h) of trimethyl ortho formate (Fluka), comprising 1.5percent by weight of montmorillonite KlO (Sd-Chemie), and 84 kg/h of ketene (ketene content about 70percent, remainder inert gases, such as N2, CO and CO2, i.e. neat ketene about 59 kg/h, that is about 1.4 kmol/h) were fed into a 620 L jet reactor (see figure 1), which had been inertized and cooled to an internal temperature of 0 0C. Under an atmosphere of nitrogen, the reaction mixture was kept at a temperature of about 0 °C and circulated in the loop via a circulating pump. Corresponding to the amount of starting materials added, and also continuously, a corresponding part of the reaction mixture flowed over into a collecting tank. After filtration, the purity of the filtrate was determined by GC as 80percent methyl 3,3-dimethoxypropionate, 8percent unreacted trimethyl orthoformate, 4percent methyl 3-methoxyprop-2-enoate and 4percent methyl acetate.By virtue of its low boiling point, it was easy to remove trimethyl orthoformate by distillation. The recovered starting material was subsequently re-cycled into the reaction mixture. <n="9"/>The yield of methyl 3,3-dimethoxypropionate was 82percent (based on conversion).
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YieldReaction ConditionsOperation in experiment
85% methanesulfonic acid; at 160℃; for 6h;Product distribution / selectivity; Example 2: Preparation of methyl 3-methoxyprop-2-enoate Under an atmosphere of nitrogen, 0.2 g (2 mmol) of methanesulfonic acid (Fluka) was added to 150 g of a filtrate, analogously obtained as described in example 1 (about 85percent, 0.86 mol of methyl 3,3-dimethoxypropionate), in a distillation apparatus with round-bottomed flask. Under constant flow of nitrogen, the mixture was slowly heated to 160 °C, and the methanol formed was directly distilled off. After 6 hours, the heat supply was stopped. The methyl 3-methoxy- prop-2-enoate obtained in this manner was 88percent pure (GC) and was purified by rectification at 10 kPa. The yield was 85 g (85percent) of methyl 3-methoxyprop-2-enoate (Ki0 kpa = 950C) with a purity of 99percent (GC).; Example 6: Preparation of methyl 3-methoxyprop-2-enoate After distillative removal of the unreacted trimethyl ortho formate from example 1, 4.4 t (30 kmol) of the methyl 3,3-dimethoxypropionate thus obtained were reacted under an atmosphere of nitrogen with 6 kg (62 mol) of methanesulfonic acid analogously to example 2. <n="10"/>Rectification at 10 kPa gave 2.4 t (21 kmol, 69percent based on trimethyl orthoformate employed) of methyl 3-methoxyprop-2-enoate (Ki0 kpa = 95 °C) in a purity of 93percent (GC).
82% With potassium hydrogensulfate; at 150 - 160℃; for 4h; In a 100 ml three-necked flask, 97 g of BJ02, 5 g of potassium bisulfate and 50 g were addedPolyethylene glycol dimethyl ether, Heated to 150 ~ 160 , 4 hours of stirring insulation, vacuum pump distillation was 46.5gMethyl 3-methoxyacrylate, Yield 82percent, GC normalized content of 98.7percent
toluene-4-sulfonic acid; In water; at 160℃; for 6h;Product distribution / selectivity; Example 3: Preparation of methyl 3-methoxyprop-2-enoate The reaction was carried out analogously to example 2 using 5 g (content 99percent, 34 mmol) of pure-distilled methyl 3,3-dimethoxypropionate and 25 mg (0.13 mmol) of/?-toluenesulfonic acid monohydrate (Fluka). The resulting crude product had a content of 91percent (GC) of methyl 3- methoxyprop-2-enoate.
4-aminobenzene sulfonic acid; at 160℃; for 6h;Product distribution / selectivity; Example 4: Preparation of methyl 3-methoxyprop-2-enoate The reaction was carried out analogously to example 2 using 5 g (content 99percent, 34 mmol) of pure-distilled methyl 3,3-dimethoxypropionate and 47 mg (0.27 mmol) of sulfanilic acid (Fluka). The resulting crude product had a content of 92percent (GC) of methyl 3-methoxyprop-2- enoate.
phosphoric acid; at 160℃; for 6h;Product distribution / selectivity; Example 5: Preparation of methyl 3-methoxyprop-2-enoate The reaction was carried out analogously to example 2 using 5 g (content 99percent, 34 mmol) of pure distilled methyl 3,3-dimethoxypropionate and 31 mg (0.31 mmol) of orthophosphoric acid (Fluka). The resulting crude product had a content of 88percent (GC) of methyl 3-methoxyprop-2- enoate.
535 g With sulfuric acid; at 190℃; for 20h; Raw material composition of this embodiment: methyl acrylate 560g, methanol 716g, cobalt oxide 2.24g, indium oxide 8.96g, concentrated sulfuric acid 17.6g;Preparation Process: Methyl acrylate, methanol and synthetic catalyst were added to the reactor and stirred well to keep the reaction liquid warm to 50°C.The reactor was filled with nitrogen and oxygen so that the partial pressures of nitrogen and oxygen were 0.4 MPa and the reaction was started. The reaction time was 16 h.When the content of methyl acrylate in the reaction solution was 3percent, the reaction was completed and the etherification reaction product was added.The etherification reaction product is filtered to recover the catalyst, petroleum ether is added to the filtrate, and the mixture is evenly stirred and allowed to stand for stratification.The upper layer is a petroleum ether layer. Atmospheric distillation recovers petroleum ether to give intermediate product methyl 3,3-dimethoxypropionate 703g.From the lower aqueous phase, methanol and methyl acrylate are recovered and applied.Separated methyl 3,3-dimethoxypropionate into the cracking kettle, then slowly added 17.6 g of concentrated sulfuric acid,The temperature was further increased to 190° C., the cleavage reaction was carried out for 20 h, and all lysates were collected to obtain 430 g of crude MAME.The crude MAME was added to the rectification vessel to recover the distillation product by vacuum distillation and weighed to obtain 478 g of the target product methyl 3-methoxyacrylate.The target product obtained in this example was 535 g, and the yield based on methyl acrylate was 82.4percent. The product purity was 95.8percent.

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  • 3,3-dimethoxy-N-(2-methyl-3-(trifluoromethyl)phenyl)propanamide [ No CAS ]
 

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