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CAS No. : | 5333-40-4 | MDL No. : | MFCD00021757 |
Formula : | C12H16O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MURZAHIYMVFXCF-UHFFFAOYSA-N |
M.W : | 208.25 | Pubchem ID : | 220116 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
65% | With sulfuric acid for 8h; Reflux; | 1.2. Synthesis of methyl 2-(2-isopropyl-5-methylphenoxy)acetate (37) 2-(2-Isopropyl-5-methylphenoxy)acetic acid (10 mmol) was dissolved in 50 mL of dried methanol, and a few drops of concentrated sulfuric acid were added. The mixture was refluxed 8 hours. Next, the solvent was evaporated, and the residue dissolved in 40 mL of ethyl acetate, washed with 0.5% NaOH and brine. The organic layer dried over anhydrous Na2SO4 and filtered. The solvent was evaporated to give the product 37. |
With sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 140 - 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water at 70 - 80℃; durch Aufloesen des Reaktionsprodukts in verd. Natronlauge und Einleiten von Kohlendioxyd; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.7% | With PPA; phosphorus pentoxide 1) 30 min, room temperature, 2) 70 deg C, 2 h; | |
60% | With PPA at 80℃; for 2h; | |
With phosphorus pentachloride; benzene Behandeln mit Aluminiumchlorid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride | ||
With thionyl chloride Heating; | ||
With thionyl chloride In tetrahydrofuran |
With thionyl chloride In dichloromethane for 4h; | 3 2-isopropyl-5-methylphenyl hydrogen carbonate (0.3g, 1.44mmol) was added to DCM (2ml) followed by the addition of thionyl chloride (4ml) in a round bottom flask. This solution was stirred for 4hrs, and then evaporated. The evaporated flask was then diluted with 4ml of DCM and then added to a solution of (3-amino-4- methoxyphenyl)(morpholino)methanone (0.3g, 1.45mmol) and in DCM (10ml) and triethylamine (0.8ml, 5.81mmol). NaHC03was added to quench the reaction followed by extraction with DCM (20ml x 3 times). The organic layers were collected and dried using MgSC . The mixture was filtered and concentrated in vacuo. The product was purified through column chromatography to form yellow oil (89mg, 14%)[00124]XH NMR (400MHz, CDCI3) d ppm 8.52 (s, 1H), 7.74-7.73 (s, 1H), 7.63-7.61 (d, 1H), 7.34-7.23 (m, 4H), 7.02-7.01 (t, 1H), 6.99-6.92(d, 2H), 4.56 (s, 2H), 3.60-3.566 (t, 2H), 3.42-3.39 (t, 2H), 1.99 (s, 1H), 1.92-1.87 (m, 4H), 1.23-1.19 (t, 1H)[00125]13C NMR (400MHz, CDCI3) d ppm 168.960, 166.525, 157.024, 138.026,136.948, 129.890, 129.053, 123.355, 122.432, 121.386, 118.985, 114.822, 67.556, 60.375, 49.598, 46.250, 26.383, 24.436, 21.039, 14.199 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium chlorate; hydrogen bromide; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With i-Amyl alcohol; iodine; iodic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 90℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium hydroxide at 95 - 100℃; for 0.166667h; Microwave irradiation; Green chemistry; | 3.2.2. MW Method General procedure: In a 50 mL flask, 1 mmol of phenol (1-15), the appropriate amount of chloroacetic acid (16) andsodium hydroxide (potassium carbonate for nipagins) were mixed.Number of moles of chloroacetic acid (16) and NaOH (K2CO3): 1.2 mmol (0.11 g) of 16 and 2.3 mmol of base for monophenols (1-9) 2.2 mmol (0.21 g) of 16 and 3.3 mmol of base for diphenols (10-12) 3.2 mmol (0.30 g) of 16 and 4.3 mmol of base for triphenols (13-15)A flask with carefully mixed solid reagents was placed in a MW-US reactor and the contentsreacted under MW conditions characterized by the following parameters: MW = 200Wat 95-100° Cfor 10min. After the process was complete, 5 mL of water was added to dissolve of solids andconcentrated hydrochloric acid was added to the reaction mixture until an acidic pH~3 was obtained,to isolate the free products. The separated precipitate was filtered off. The main product was purifiedby crystallization or column chromatography using a mixture of chloroform and methanol (9:1 or 5:1)as an eluent. |
87% | Stage #1: thymol With sodium hydroxide In water monomer at 50℃; for 0.5h; Stage #2: chloroacetic acid In water monomer at 50℃; Stage #3: With sulfuric acid | Phenoxy Acid Synthesis General procedure: A phenol compound (thymol, carvacrol, eugenol, vanilin) dissolved in warm waterwas added to a solution of sodium hydroxide (2.1 eq.) in warm water. After mixing for30 min at 50 C, monochloroacetic acid (2.1 eq.) was added. The obtained solution wasmixed overnight at 50 C. After cooling to room temperature, the solution was acidified topH 2 with 10% sulfuric acid. The obtained solid phenoxy acetic acid was separated witha Buchner funnel. Water from the aqueous phase was removed on a rotary evaporator,and the residue was dissolved in hot toluene and washed with water. After separationfrom the organic phase, phenoxyacetic acid was precipitated and separated with a Buchnerfunnel. The combined crude phenoxyacids were dissolved in hot toluene, and activatedcharcoal was added and mixed for 15 min at 50 C. After removing the charcoal from thehot solution, the organic phase was cooled to room temperature, and the obtained solidphenoxyacetic acid was filtrated and dried in vacuum. |
50% | With sodium hydroxide In water monomer for 3h; Heating; |
32% | With sodium hydroxide In water monomer Reflux; | 3 General Procedure 3: Chloroacetic Acid Coupling General procedure: In a round bottom flask equipped with a magnetic stirrer, selected alcohol(1.1 equiv.) was dissolved in dhhO with chloroacetic acid (1 equiv.). Solid NaOH (3 equiv.) was then added to the flask and the reaction was brought to reflux. Once the reaction was deemed complete by TLC analysis, the mixture was cooled to room temperature and carefully acidified with concentrated HCI. The product was filtered off from the solvent and purified by recrystallization (Ethyl Acetate and Hexanes). The product was then characterized by NMR analysis. This compound was prepared following general procedure 3 using Thymol (34.9 g. 232.8 mmol), chloroacetic acid (20 g, 211.7 mmol), and NaOH (25.4 g, 635 mmol) in distilled H2O (75 mL).[00154] No purification was required for this reaction. Pure product, 2-(2-isopropyl-5methylphenoxy)acetic acid, a beigh powder (14.23 g, 32%, Rf= 0.57 in 3:2 EtOAc : Hexanes).1H NMR (400 MHz; CDCI3): d 7.15 (d, J = 7.7, 1H), 6.83 (d, J = 7.7, 1H), 6.58 (s, 1H), 4.70 (s, 2H), 3.36 (7, J = 6.9, 1H), 2.33 (s, 3H), 1.24 (d, J = 6.9, 6H).13C NMR: (400 MHz; CDCI3): d 174.85, 155.01, 136.91, 135.01, 126.85,123.12, 112.84, 65.63, 27.03, 23.25, 21.74 |
29% | Stage #1: thymol; chloroacetic acid With sodium hydroxide In water monomer at 120℃; for 3h; Heating / reflux; Stage #2: In water monomer at 20℃; Acidic conditions; | 7 NaOH beads (66.6 mmol) dissolved in water were added to a mixture of thymol 20 (33.3 mmol), chloroacetic acid 21 (33.3 mmol) and water. The mixture was refluxed at 120 °C for 3 h. The mixture was cooled to room temperature, acidified, extracted with diethyl ether and washed. The solvent was evaporated thus giving precipitated thymolacetic acid 22 with a yield of 29 %. Betulin 1 (7.2 mmol), thymolacetic acid 22 (7.2 mmol), and toluene (80 ml) were heated to 160 °C, followed by the addition of isopropyl titanate (1.4 mmol) to the reaction mixture. The reaction mixture was refluxed for 4.5 h untill all water was separated by the water separation tube. The mixture was cooled to room temperature and the precipitate formed was filtered. The organic phase was washed and the solvent was evaporated. The crude product was recrystallized from boiling solution of cyclohexane and toluene (3.5:1), thus giving 28-carboxymethoxythymol ester of betulin 23 (yield: 61 %) as the reaction product. |
29% | Stage #1: thymol; chloroacetic acid With sodium hydroxide In water monomer at 120℃; for 3h; Stage #2: In water monomer at 20℃; Acidic conditions; | 7 NaOH beads (66.6 mmol), dissolved in water, were added to a mixture of thymol 20 (33.3 mmol), chloroacetic acid 21 (33.3 mmol) and water. The mixture was refluxed at 120 °C for 3 h. The mixture was cooled to room temperature, acidified, extracted with diethyl ether and washed. The solvent was evaporated thus giving precipitated thymolacetic acid 22 with a yield of 29 %. Betulin 1 (7.2 mmol), thymolacetic acid 22 (7.2 mmol), and toluene (80 ml) were heated to 160 °C, followed by the addition of isopropyl titanate (1.4 mmol) to the reaction mixture. The reaction mixture was refluxed for 4.5 h until all water was separated by water separation tube. The mixture was cooled to room temperature and the pre- cipitate formed was filtered. The organic phase was washed and the solvent was 07 Aug 200736evaporated. The crude product was recrystallized from boiling solution of cyclo- hexane and toluene (3.5:1), thus giving 28-carboxymethoxythymol ester of betulin 23 with a yield of 61 %. |
11% | With sodium hydroxide In water monomer at 100℃; for 2h; Inert atmosphere; | |
With sodium hydroxide | ||
With sodium hydroxide | ||
With sodium hydroxide | ||
With sodium hydroxide for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 170℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride In carbon disulfide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium hydroxide for 0.0833333h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In toluene at 160℃; for 4.5h; | 7 NaOH beads (66.6 mmol), dissolved in water, were added to a mixture of thymol 20 (33.3 mmol), chloroacetic acid 21 (33.3 mmol) and water. The mixture was refluxed at 120 °C for 3 h. The mixture was cooled to room temperature, acidified, extracted with diethyl ether and washed. The solvent was evaporated thus giving precipitated thymolacetic acid 22 with a yield of 29 %. Betulin 1 (7.2 mmol), thymolacetic acid 22 (7.2 mmol), and toluene (80 ml) were heated to 160 °C, followed by the addition of isopropyl titanate (1.4 mmol) to the reaction mixture. The reaction mixture was refluxed for 4.5 h until all water was separated by water separation tube. The mixture was cooled to room temperature and the pre- cipitate formed was filtered. The organic phase was washed and the solvent was 07 Aug 200736evaporated. The crude product was recrystallized from boiling solution of cyclo- hexane and toluene (3.5:1), thus giving 28-carboxymethoxythymol ester of betulin 23 with a yield of 61 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In toluene at 160℃; for 4.5h; Heating / reflux; | 7 NaOH beads (66.6 mmol) dissolved in water were added to a mixture of thymol 20 (33.3 mmol), chloroacetic acid 21 (33.3 mmol) and water. The mixture was refluxed at 120 °C for 3 h. The mixture was cooled to room temperature, acidified, extracted with diethyl ether and washed. The solvent was evaporated thus giving precipitated thymolacetic acid 22 with a yield of 29 %. Betulin 1 (7.2 mmol), thymolacetic acid 22 (7.2 mmol), and toluene (80 ml) were heated to 160 °C, followed by the addition of isopropyl titanate (1.4 mmol) to the reaction mixture. The reaction mixture was refluxed for 4.5 h untill all water was separated by the water separation tube. The mixture was cooled to room temperature and the precipitate formed was filtered. The organic phase was washed and the solvent was evaporated. The crude product was recrystallized from boiling solution of cyclohexane and toluene (3.5:1), thus giving 28-carboxymethoxythymol ester of betulin 23 (yield: 61 %) as the reaction product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 60 percent / polyphosphoric acid / 2 h / 80 °C 2: 73 percent / 1M NaOMe / methanol / 6 h / Heating 3: 69 percent / 2N NaOH / methanol / 6 h / Heating 4: 82 percent / Zn/Hg, conc. HCl / toluene / 26 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 60 percent / polyphosphoric acid / 2 h / 80 °C 2: 73 percent / 1M NaOMe / methanol / 6 h / Heating 3: 69 percent / 2N NaOH / methanol / 6 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 60 percent / polyphosphoric acid / 2 h / 80 °C 2: 73 percent / 1M NaOMe / methanol / 6 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 2: 60 percent / NEt3 / CH2Cl2 / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 2: 50 percent / NEt3 / CH2Cl2 / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 61.2 percent / K2CO3 / acetone / 18 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 59 percent / dioxane / 7 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 61.2 percent / K2CO3 / acetone / 18 h / Heating 3: 67 percent / ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 59 percent / dioxane / 7 h / Heating 3: NaOAc, glacial acetic acid / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 61.2 percent / K2CO3 / acetone / 18 h / Heating 3: 61 percent / ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 59 percent / dioxane / 7 h / Heating 3: 80 percent / NaOAc, glacial acetic acid / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 61.2 percent / K2CO3 / acetone / 18 h / Heating 3: 73.9 percent / ethanol / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 59 percent / dioxane / 7 h / Heating 3: 75 percent / NaOAc, glacial acetic acid / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 59 percent / dioxane / 7 h / Heating 3: 69 percent / NaOAc, glacial acetic acid / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 61.2 percent / K2CO3 / acetone / 18 h / Heating 3: 58 percent / ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 61.2 percent / K2CO3 / acetone / 18 h / Heating 3: 63 percent / ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 59 percent / dioxane / 7 h / Heating 3: 60 percent / NaOAc, glacial acetic acid / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 59 percent / dioxane / 7 h / Heating 3: 72 percent / NaOAc, glacial acetic acid / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 61.7 percent / polyphosphoric acid, P2O5 / 1) 30 min, room temperature, 2) 70 deg C, 2 h 2: 59 percent / dioxane / 7 h / Heating 3: 64 percent / NaOAc, glacial acetic acid / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 2: aluminium chloride; carbon disulfide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2 2: aluminium chloride; carbon disulfide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2 2: aluminium chloride; carbon disulfide 3: ethanol; aq. NaOH solution |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: 100 - 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / Heating 2: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / Heating 2: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / tetrahydrofuran 2: Py / dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: 2-isopropyl-5-methylphenoxyacetic acid With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Heating; Stage #2: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / 8 h / Reflux 2: sodium / methanol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | Stage #1: 2-isopropyl-5-methylphenoxyacetic acid; benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride With benzotriazol-1-ol; triethylamine In dichloromethane at 0 - 25℃; for 0.25h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51 %Spectr. | With triethylamine pentahydrogen fluoride salt; 2,4,6-trimethyl-pyridine In dichloromethane at 20℃; Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 4 h 2: triethylamine / dichloromethane |
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