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Chemical Structure| 551-08-6
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Product Details of [ 551-08-6 ]

CAS No. :551-08-6 MDL No. :MFCD00047319
Formula : C12H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WMBOCUXXNSOQHM-FLIBITNWSA-N
M.W : 188.22 Pubchem ID :642376
Synonyms :
Butylidenephthalide;NSC 325307;BP;(Z)-Butylidenephthalide;n-Butylidenephthalide

Safety of [ 551-08-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 551-08-6 ]

* 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 [ 551-08-6 ]

[ 551-08-6 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 85-44-9 ]
  • [ 2082-59-9 ]
  • [ 551-08-6 ]
YieldReaction ConditionsOperation in experiment
76.1% With sodium valerate at 170 - 190℃; for 4h; 1; 4 Example 4 Preparation and distillation of butenephthalide (DBT-1) 441.41 g of pentanoic acid anhydride,Phthalic anhydride 386.59g,Sodium valerate 117.81g, added to the 5L reaction flask,Stir well and mix well,Heated to about 170 for 1h;Followed by additional sodium valerate 118.00g, and then warmed to about 190 , the reaction was continued warm 3h; the reaction completed, the system was cooled to about 100 , dropping 1L deionized water, heating was continued to return,Continue to reflow 1h, cooling, down to room temperature; control system temperature at about 25 ,The mixture was adjusted to pH 9 with concentrated aqueous ammonia, extracted three times with 2.5 L of dichloromethane, washed twice with 1 L of dilute ammonia (1%), twice with 1 L of deionized water and dried with 100 g of anhydrous calcium chloride, filtered with suction to remove the desiccant , Concentrated dichloromethane recovery, was dark red oily liquid, 20cm long thorn-type distillation column vacuum distillation,Collected 140 ~ 145 / 2 ~ 3mmHg distillate to obtain 339.66g yellow oily liquid, namely, butylene phthalide (DBT-1).
With sodium valerate
With sodium acetate at 200℃; for 3h; 1 In a 500 ml reaction flask, 60.0 g of phthalic anhydride was charged,Valeric anhydride 113. 2 g,Anhydrous sodium acetate 33. 23 g,Heating to 200 ° C reaction 3h,After the reaction was completed, the n-pentanoic acid was recovered by concentration under reduced pressure, and the temperature was lowered to 30 ° C. Sodium borohydride sodium hydroxide solution (6. 5 g sodium borohydride, 40.0 g sodium hydroxide in 100 ml of water) was slowly added, Reaction 5h, the reaction finished dichloromethane burning impurities, the aqueous phase with dilute hydrochloric acid to adjust the pH to 1,85 ° C insulation 3h, after cooling, dichloromethane extraction, concentration was n-butyl phthalide 54. 2g, yield 70 , And the purity of liquid was 98.36%.
45 kg With sodium acetate at 300℃; for 4h; Large scale; 1.1 (1) Preparation of butenylphthalide Phthalic anhydride 148.0 Kg,Anhydrous sodium acetate 82.0Kgwith300.0 L of n-valeric anhydride was heated at 300 ° C for 4 hours, and the residue of the low boiling fraction (controlled at 150 ° C or lower) was distilled off with hot water and then neutralized with NaHCO3 to a pH of 6 to 7,Extracted with 7 × 500L ether, combined with organic layer, anhydrous Na2SO4 dry, remove the desiccant,Evaporation of ether, silica gel column chromatography, chloroform - petroleum ether elution, to obtain butene phthalide 45.0Kg.
45 kg With sodium acetate at 300℃; for 4h; Large scale; 1.1 (1) Preparation of butene-phthalide Phthalic anhydride 148.0Kg,Anhydrous sodium acetate 82.0Kg and n-valeric anhydride 300.0L at 300 ° CHeated back to reflux for 4 h,Distill off the low boiling fraction (controlled below 150 ° C),The residue is dissolved in hot water,Neutralize with NaHCO3 to pH=6-7,Extracted with 7 x 500 L of diethyl ether.The organic layers were combined, dried over anhydrous Na 2 SO 4 and filtered to remove desiccant.Evaporate the ether,Silica gel column chromatography, elution with chloroform-petroleum etherTo obtain butene phthalide 45.0Kg

  • 2
  • [ 85-44-9 ]
  • [ 3431-67-2 ]
  • [ 551-08-6 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether Erwaermen des Reaktionsprodukts mit Schwefelsaeure;
  • 6
  • [ 551-08-6 ]
  • 2-valeryl-benzoic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonia
  • 7
  • [ 551-08-6 ]
  • [ 3553-34-2 ]
YieldReaction ConditionsOperation in experiment
With acetic acid; platinum at 70℃; Hydrogenation;
  • 8
  • [ 551-08-6 ]
  • [ 3413-15-8 ]
YieldReaction ConditionsOperation in experiment
97% With 5%-palladium/activated carbon; hydrogen; In ethanol; at 20℃; under 3750.38 Torr;Autoclave; General procedure: Compound Pre 1 (1.2 g), 5% Pd/C (0.12 g, 10% wt) and anhydrous EtOH (40 mL) were charged in a 200 mL-autoclave. The autoclave was flushed and then pressurized with H2 to 0.5 MPa, the mixture was stirred at room temperature for 6-10 h. The mixture vented to discharge the excess H2. After filtration, solvent was removed under reduced pressure and the crude residue was purified by column chromatography on silica gel with petroleum ether-ethyl acetate as the eluent to afford the desired product.
54.2 g With sodium tetrahydroborate; sodium hydroxide; In water; at 30 - 60℃; for 5h; In a 500 ml reaction flask, 60.0 g of phthalic anhydride was charged,Valeric anhydride 113. 2 g,Anhydrous sodium acetate 33. 23 g,Heating to 200 C reaction 3h,After the reaction was completed, the n-pentanoic acid was recovered by concentration under reduced pressure, and the temperature was lowered to 30 C. Sodium borohydride sodium hydroxide solution (6. 5 g sodium borohydride, 40.0 g sodium hydroxide in 100 ml of water) was slowly added, Reaction 5h, the reaction finished dichloromethane burning impurities, the aqueous phase with dilute hydrochloric acid to adjust the pH to 1,85 C insulation 3h, after cooling, dichloromethane extraction, concentration was n-butyl phthalide 54. 2g, yield 70 , And the purity of liquid was 98.36%.
43 kg With palladium 10% on activated carbon; hydrogen; In diethyl ether; at 20℃; for 24h;Large scale; 3-Butene Phthalide45.0Kg dissolved in ether, add 4.5Kg 10% Pd / C, with H2 gas replacement 6 times, filling H2, stirring, The reaction was carried out at room temperature for 24 h. After Pd / C was filtered off, the residue was purified by silica gel column chromatography and chloroform-petroleum ether to give 43.0 Kg of butylphthalide.
With C31H34IrNOP(1+)*C32H12BF24(1-); hydrogen; In dichloromethane; at 25℃; under 38002.6 Torr; for 24h;Autoclave; Glovebox; Green chemistry; Under a argon atmosphere, 0.002 mmol of a ruthenium complex and 0.2 mmol of a phenylhydrazine derivative substrate were added to a 10 mL hydrogenation flask, and after evacuation, 2.0 mL of dichloromethane was added. The system was placed in an autoclave in a glove box. After replacing the hydrogen three times in the autoclave, it was charged to the corresponding reaction pressure and reacted at 25 C for 24 h. After the end of the reaction, hydrogen was carefully evolved, and a small amount of the sample was subjected to 1H NMR to judge the conversion. The reaction system was filtered through a short silica gel column to remove the metal, and the enantioselectivity of the product was determined by high performance liquid phase. The yield and ee values are shown in Table 2 (negative values indicate opposite product configurations).
With palladium 10% on activated carbon; hydrogen; In diethyl ether; at 20℃; for 24h; 3-Butylidenephthalide 45.0KgSoluble in ether, add 4.5Kg 10% Pd/C,Replace 6 times with H2 gas, charge with H2, stir, and react at room temperature for 24 hours.After filtering off Pd/C, concentration, silica gel column chromatography, elution with chloroform-petroleum ether,The butylphthalide was obtained in 43.0 Kg.We conducted quality research on the obtained APIs andAccelerated stability studies at (40 C, 75% RH),The results are shown in Table 1.

  • 9
  • [ 201230-82-2 ]
  • [ 79784-61-5 ]
  • [ 551-08-6 ]
YieldReaction ConditionsOperation in experiment
87% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 100℃; for 3h;
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  • [ 20871-40-3 ]
YieldReaction ConditionsOperation in experiment
80% With 3THF*Mg2Cl2OTiNCO In various solvent(s) at 120℃; for 24h;
80% With 1-methyl-pyrrolidin-2-one; 3THF*Mg2Cl2O*Ti-NCO at 120℃; for 24h;
  • 11
  • [ 85-44-9 ]
  • [ 551-08-6 ]
YieldReaction ConditionsOperation in experiment
With sodium valerate at 170℃;
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  • [ 79784-61-5 ]
  • [ 20871-40-3 ]
  • [ 551-08-6 ]
YieldReaction ConditionsOperation in experiment
59% With 1-methyl-pyrrolidin-2-one; tetrakis(triphenylphosphine) palladium(0); potassium carbonate at 100℃; for 16h;
  • 13
  • [ 551-08-6 ]
  • [ 122654-56-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanolic KOH-solution 2: ethanol; N2H4+H2O 3: hydrochloric acid; water; zinc
  • 14
  • [ 551-08-6 ]
  • [ 64624-87-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanolic KOH-solution 2: sulfuric acid
  • 15
  • [ 551-08-6 ]
  • [ 100134-54-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanolic KOH-solution 2: ethanol; N2H4+H2O
  • 16
  • [ 551-08-6 ]
  • 3-butyl-6-nitro-2-benzofuran-1(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Raney nickel; ethanol 2: sulfuric acid; nitric acid
Multi-step reaction with 2 steps 1: platinum; acetic acid / Hydrogenation 2: sulfuric acid; nitric acid
  • 17
  • [ 551-08-6 ]
  • 4-butyl-1-oxo-1<i>H</i>-phthalazine-2-carboxylic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanolic KOH-solution 2: ethanol; sodium acetate; H2O
  • 18
  • [ 551-08-6 ]
  • [ 380905-48-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanolic KOH-solution 2: platinum; acetic acid / Hydrogenation.Behandlung des danach erhaltenen 3-Butyl-phthalids mit aethanol. Kalilauge
Stage #1: 3-butylidenephthalide With ethanol; hydrogen at 25 - 35℃; for 3h; Stage #2: With sodium hydroxide In lithium hydroxide monohydrate at 50 - 60℃; for 2h; 5 Example 5 Preparation of Hydroxypentyl Benzoic Acid (DBT-2) To the hydrogenation reactor was added anhydrous ethanol 1300mL,Butenephthalide (DBT-1) 325.00 g,Join Raney nickel (wet) 48.75g,Perform 4 times hydrogen exchange to eliminate air.The temperature is heated to 25 ~ 35 ,Pressure control 2.5 atmospheres (2.5kg / cm2) hydrogenation reaction,Until not hydrogen absorption so far, about 3h; remove the catalyst, concentration of ethanol under reduced pressure,Obtained pale yellow oily liquid is the first intermediate, purity 97.893%.To 3L reaction flask was added 1600ml of deionized water, sodium hydroxide 71.20g,Stirring to dissolve, adding above light yellow oily liquid,Temperature control 50 ~ 60 , the reaction of about 2h; completion of the reaction,Cooled to about 20 with 1600ml dichloromethane extracted three times,Add 160mL anhydrous ethanol in the aqueous phase, adjust pH = 6 with glacial acetic acid, suction filtration,The filter cake was washed with 160 ml of water to give the second intermediate(DBT-2).
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C 2: potassium hydroxide; lithium hydroxide monohydrate / ethanol
  • 19
  • [ 551-08-6 ]
  • 2-(1-semicarbazono-pentyl)-benzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanolic KOH-solution 2: sulfuric acid 3: sodium acetate; aqueous ethanol
  • 20
  • [ 551-08-6 ]
  • [ 76681-73-7 ]
  • [ 72917-31-8 ]
YieldReaction ConditionsOperation in experiment
Resolution of racemate; The roots of Angelicae sinensis (Oliv.) were supplied from Chung-Yuan Co., Taipei, Taiwan and were identified by Professor Han-Ching Lin. A voucher of herbarium specimen was deposited at the School of Pharmacy, National Defense Medical Center. The dried and powdered rhizomes of Angelicae sinensis (12 kg) were extracted 3 times with acetone (24 L/time) to give acetone extract called as AS-A. AS-A was then subjected to chloroform extraction 3 times (24 L/times). The latter extracts were concentrated under reduced pressure to yield 31.67 g of chloroform extract, called as AS-C (from 100g of acetone extract). A hexane extract (AS-H) was obtained by extracting AS-A with hexanes. n-Butylidenephthalide (BP) was purchased from Lancaster Synthesis Ltd. (Newgate, Morecambe, UK) and used without further purification. E- and Z-forms of BP were separated with column chromatography and characterized with HPLC and NMR. They were dissolved in DMSO, incubated with shaking at 25°C for 1 hour and stored at 4°C before each in vitro experiment.
  • 21
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  • [ 109-52-4 ]
  • [ 551-08-6 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate at 240℃; for 1h;
  • 22
  • [ 551-08-6 ]
  • [ 91764-79-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5%-palladium/activated carbon; hydrogen / ethanol / 20 °C / 3750.38 Torr / Autoclave 2: phenylsilane; potassium hydroxide / tetrahydrofuran / 4 h / Schlenk technique; Inert atmosphere; Reflux
  • 23
  • [ 551-08-6 ]
  • [ 3413-15-8 ]
  • [ 125412-70-6 ]
YieldReaction ConditionsOperation in experiment
81 % ee With C30H44IrNO2P(1+)*C32H12BF24(1-); hydrogen In dichloromethane at 25℃; for 24h; Autoclave; Glovebox; Green chemistry; enantioselective reaction; 2 Example 2: Synthesis of 2a Under a argon atmosphere, 0.002 mmol of a ruthenium complex and 0.2 mmol of a phenylhydrazine derivative substrate were added to a 10 mL hydrogenation flask, and after evacuation, 2.0 mL of dichloromethane was added. The system was placed in an autoclave in a glove box. After replacing the hydrogen three times in the autoclave, it was charged to the corresponding reaction pressure and reacted at 25 ° C for 24 h. After the end of the reaction, hydrogen was carefully evolved, and a small amount of the sample was subjected to 1H NMR to judge the conversion. The reaction system was filtered through a short silica gel column to remove the metal, and the enantioselectivity of the product was determined by high performance liquid phase. The yield and ee values are shown in Table 2 (negative values indicate opposite product configurations).
88 % ee With R,S-[Ir(1,5-cyclooctadiene)(PPh2(C9H10)(C3H3NO-tBu))] tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; hydrogen In dichloromethane at 25℃; for 24h; Autoclave; Glovebox; Green chemistry; enantioselective reaction; 2 Example 2: Synthesis of 2a Under a argon atmosphere, 0.002 mmol of a ruthenium complex and 0.2 mmol of a phenylhydrazine derivative substrate were added to a 10 mL hydrogenation flask, and after evacuation, 2.0 mL of dichloromethane was added. The system was placed in an autoclave in a glove box. After replacing the hydrogen three times in the autoclave, it was charged to the corresponding reaction pressure and reacted at 25 ° C for 24 h. After the end of the reaction, hydrogen was carefully evolved, and a small amount of the sample was subjected to 1H NMR to judge the conversion. The reaction system was filtered through a short silica gel column to remove the metal, and the enantioselectivity of the product was determined by high performance liquid phase. The yield and ee values are shown in Table 2 (negative values indicate opposite product configurations).
With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; water; (2S,4S)-2,4-bis(diphenylphosphino)pentane; copper(ll) bromide; zinc In chlorobenzene at 60℃; Inert atmosphere; Schlenk technique; Overall yield = 80 percent; Overall yield = 30.4 mg; Optical yield = 84 percent ee; 3 Example 3 Under an argon atmosphere, Rh(COD)2OTf, (S,S)-BDPP and 1.0 mL of chlorobenzene were added to a Schlenk tube equipped with a magnetic stir bar.The resulting solution was stirred at room temperature for 30 minutes, copper bromide was added and stirred for 10 minutes, and a solution of 3-butylene isobenzofuran-1(3H)-one in chlorobenzene (1.0 mL) was added to the above mixture.After adding H2O, the mixture was stirred at 60°C and monitored by TLC until 3-butylene isobenzofuran-1(3H)-one was completely consumed.Among them, the molar ratio of 3-butylene isobenzofuran-1(3H)-one, Rh(COD)2OTf, (S,S)-BDPP, copper bromide, Zn powder, H2O is 1:0.045:0.1:0.2 : 4:25. The residue was purified by silica gel column chromatography to obtain the product 3-butylisobenzofuran-1(3H)-one, as a colorless oil, 30.4 mg, yield 80%, ee value 84%.
  • 24
  • [ 551-08-6 ]
  • [ 125412-70-6 ]
YieldReaction ConditionsOperation in experiment
98% With C38H48IrNOP(1+)*C32H12BF24(1-); hydrogen In dichloromethane at 25℃; for 24h; Autoclave; Glovebox; Green chemistry; enantioselective reaction; 4 Example 4: Synthesis of 2a Under a argon atmosphere, 0.005 mmol of ruthenium complex 1a and 0.4 mmol of phenylhydrazine derivative substrate were added to a 10 mL hydrogenation flask, and after evacuation, 2.0 mL of dichloromethane was added. The system was placed in an autoclave in a glove box. After replacing the hydrogen three times in the autoclave, it was charged to 10 atm and reacted at 25 ° C for 24 h. After the end of the reaction, hydrogen was carefully evolved, and a small amount of the sample was subjected to 1H NMR to judge the conversion. The reaction system was concentrated and purified by flash column chromatography to give the corresponding phenylhydrazine compound 2a, yield 98%, ee 95%.
  • 25
  • [ 551-08-6 ]
  • [ 765-30-0 ]
  • C15H19NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran at 20℃; for 6h; 2 Example 2: Synthesis of N-cyclopropyl-3-n-butyl-3-hydroxy-phthalide lactam. The ligustilide (1.880 g, 0.010 mol) was dissolved in 50 mL of tetrahydrofuran, and the cyclopropylamine (0.684 g, 0.012 mol) was dissolved in 20 mL of tetrahydrofuran. The tetrahydrofuran solution of cyclopropylamine was added dropwise under mechanical stirring at room temperature. To the solution of ligustilide in tetrahydrofuran, the reaction was stirred for 6 h, and the tetrahydrofuran and excess cyclopropylamine solution were recovered by rotary distillation. 200 mL of petroleum ether was added to the above concentrate, and the mixture was uniformly mixed. Out, suction filtration, the crude product was 2.083 g, the reaction yield was 85%.The crude product was recrystallized from a mixed solvent of petroleum ether and acetone (10:1, V/V) to give a crystal product of 1.666 g. Using the HPLC-DAD method, the area normalized content was determined to be 99.6%.The target compound was detected as the target compound by MS, NMR and X-Ray single crystal diffraction techniques (see Figures 8, 10, 11, 12), and the chiral separation of the compound was determined by chiral separation of high performance liquid chromatography. Structure (see Figure 13).
  • 26
  • [ 162050-42-2 ]
  • [ 551-08-6 ]
YieldReaction ConditionsOperation in experiment
26.8 g With toluene-4-sulfonic acid In toluene for 3h; Reflux; 1 Take the product of the previous step 3-hydroxy-3-butyl-1(3H)-isobenzofuranone 29.8g and add to100mL toluene, then add 15g of p-toluenesulfonic acid, reflux water separation reaction for 3h,The reaction solution was washed twice with a small amount of saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, and distilled off toluene to obtain crude 3-n-butenylphthalide,Distillation yielded 26.8g of pure 3-n-butenylphthalide with a yield of 71.28%.The purity by gas chromatography was 99.2%.
  • 27
  • [ 85-44-9 ]
  • [ 2082-59-9 ]
  • [ 6106-41-8 ]
  • [ 551-08-6 ]
YieldReaction ConditionsOperation in experiment
at 135 - 185℃; for 0.4h; 1; 5 Preparation of Compound II Add compound I (148g, 1mol), valeric anhydride (279g, 1.5mol), and sodium valerate (62g, 0.5mol) into a 1L three-necked flask. Under mechanical stirring, increase the temperature to 135145 for reaction. Until no gas is generated, react for about 3 hours; then add sodium valerate (62g, 0.5mol) to the system, raise the temperature to 175185°C, keep the temperature for 1 hour, and detect by HPLC. The reaction of the raw materials was complete (1.5% of compound 1 remained). After the reaction is complete, Lower the temperature of the system to 90-100°C, remove the low-boiling reagents by distillation under reduced pressure to obtain a reddish brown concentrate, then lower the temperature of the system to room temperature, and add 450g of purified water to the concentrate. Adjust the pH of the system to 8-9 with ammonia water, extract twice with 450ml of dichloromethane, Wash twice with 450g of saturated brine, remove the solvent under reduced pressure to obtain a reddish brown oily liquid, Vacuum distillation collects the fraction at 140180/510mmHg, 150g of light yellow oily liquid is obtained, which is compound II, and its (Z/E) purity is 86.79%, Yield 79%
  • 28
  • [ 551-08-6 ]
  • sodium 2-(α-n-pentanoyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide In methanol at 25 - 35℃; for 1h; 2; 6 Preparation of compound III (M1 is sodium ion) Add 600g of methanol and 33.2g of sodium hydroxide into a 2L three-necked flask, and dissolve under stirring. 120 g of compound II prepared in Example 1 was added dropwise to it, after the dripping was completed, the reaction was carried out at 25°C to 35°C for 1 hour, and the reaction of the raw materials was complete (Compound II was not detected) by HPLC. Reduce the temperature of the system to 010, add 720g of methyl tert-butyl ether dropwise to it, After the dripping is completed, keep the temperature for 2 hours, and filter with suction. The filter cake is vacuum dried at 40°C to obtain 131g of light orange solid, which is compound III (M1 is sodium ion) with a purity of 99.36%. The maximum single impurity is 0.19%, and the yield is 90%.
90.5% With sodium hydroxide In lithium hydroxide monohydrate for 1h; Reflux; 1; 5 Example 1 At room temperature, the mass concentration of 11.15mL was added to the reaction flask with an aqueous sodium hydroxide solution of 11%, then weighed 5.25g of the compound of formula II structure, heated to reflux for 1 hour; carried out TLC detection (thin layer chromatography) , in the detection process, the volume ratio of ethyl acetate: petroleum ether=1:2, to determine whether the reaction is completed); after the detection reaction is completed, it is lowered to room temperature, and the obtained reaction product is concentrated to dryness at 55 ° C under reduced pressure, and obtained after the concentration 50 mL of dichloromethane was added to the product to make a slurry for 0.5 hours; the slurry was filtered and dried to obtain 5.76 g of a white solid product (yield 90.5%).
  • 29
  • [ 551-08-6 ]
  • (R/S)-2-(1-hydroxy-n-pentyl)benzoic acid potassium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / methanol / 1 h / 25 - 35 °C 2.1: sodium tetrahydroborate; sodium hydroxide / water / 2 h / 0 - 100 °C 2.2: 2 h / 60 - 70 °C
  • 30
  • [ 551-08-6 ]
  • C16H20O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C 2: potassium hydroxide; lithium hydroxide monohydrate / ethanol 3: 4-dimethylaminopyridine; triethylamine / ethyl acetate
  • 31
  • [ 551-08-6 ]
  • [ 3413-15-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C 2.1: potassium hydroxide; lithium hydroxide monohydrate / methanol / 1 h / 60 °C 2.2: -10 - 20 °C / pH 3 - 4
Same Skeleton Products
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