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CAS No. : | 24539-92-2 | MDL No. : | MFCD00053308 |
Formula : | C10H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GSTOHKXQBZZTPF-UHFFFAOYSA-N |
M.W : | 164.20 | Pubchem ID : | 2758850 |
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 |
---|---|---|
96% | With aluminium trichloride 1.) 70 -> 80 deg C, 2 h, 2.) 120 deg C, 40 min; | |
90% | With aluminium trichloride | |
66.7% | With aluminum (III) chloride at 130℃; for 2h; | 22 Intermediate 55: 1 -(5-ethyl-2-hydroxyphenyl)ethanone To aluminium trichloride (5.07 g, 38.0 mmol) was added 4-ethylphenyl acetate (3.28 g, 20 mmol) dropwise. The mixture was heated to 130 °C for 120 minutes then cooled. The yellow oil was slowly poured into water and extracted with EtOAc (2x80 ml). The combined organic layers were washed with brine, then dried over MgS04 and concentrated in vacuo to give a yellow oil. The oil was purified by silica gel chromatography (hexane/EtOAc = 10/1 ) to obtain the title compound 1 -(5-ethyl-2-hydroxyphenyl)ethanone (2.33 g, 13.34 mmol, 66.7 % yield) as a pale yellow oil. m/z: [M + H]+ Calcd for C10H13O2 165.1 ; Found 164 |
20.1% | With aluminum (III) chloride In dichloromethane for 10h; Cooling with ice; Reflux; | |
With aluminium trichloride | ||
With aluminium trichloride at 140℃; for 0.25h; Yield given; | ||
With aluminium trichloride | ||
Stage #1: p-ethylphenyl acetate With aluminum (III) chloride at 120℃; for 6h; Stage #2: With water Cooling; | 2 Synthesis of substituted o-hydroxyacetophenone General procedure: Powdered anhydrous AlCl3 (186 g, 1.4 mol) was added little by little to acetic acid phenyl ester b1 (95.3 g, 0.7 mol) in a round-bottomed flask in an ice-water bath. The resultant mixture was heated to 120 °C for 6 h in an oil bath. Then the reaction mixture was added a lot of crushed ice for hydrolysis. The new formed organic layer in the reaction mixture was extracted by EtOAc, dried over anhydrous Na2SO4, and filtered off by suction filtration. The solvent was removed under reduced pressure to give the crude product, which was then purified by chromatography on silica using petroleum ether/ethyl acetate as the eluent. o-hydroxyacetophenone c1 (20.1 g, 21%) was obtained | |
With aluminum (III) chloride at 120℃; | ||
77.a 6-Ethyl-4-(N-Ethylsulfonyl-N-Methyl)Amino-2,2-Dimethyl-Chroman a) 5-Ethyl-2-hydroxyacetophenone is obtained analogously to the procedure indicated in Example 63 b) from 4-ethylphenyl acetate and anhydrous, active aluminum chloride. Slightly yellowish-colored oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With nitric acid In acetic acid for 2.5h; Ambient temperature; | |
44% | With sulfuric acid; nitric acid at -20℃; | |
With sulfuric acid; nitric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With pyridine; hydroxylamine hydrochloride In methanol for 5h; Heating; | |
With pyridine; hydroxylamine hydrochloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With aluminium trichloride In 1,2-dichloro-ethane at 110 - 120℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In tetrahydrofuran 0 deg C, 5 min and 65 deg C, 20 min; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With pyridine at 50℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With trichlorophosphate In pyridine at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With potassium hydroxide In ethanol at 20℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With titanium tetrachloride In dichloromethane at -78 - 20℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine 2: AlCl3 | ||
Multi-step reaction with 2 steps 1: 95 percent / NaOH 2: 90 percent / AlCl3 | ||
Multi-step reaction with 2 steps 1.1: sulfuric acid / 0.17 h / 20 °C 2.1: aluminum (III) chloride / 6 h / 120 °C 2.2: Cooling |
Multi-step reaction with 2 steps 1: sulfuric acid / 20 °C 2: aluminum (III) chloride / 120 °C | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 0.33 h / 20 °C 2: aluminum (III) chloride / dichloromethane / 10 h / Cooling with ice; Reflux | ||
Multi-step reaction with 2 steps 1: acetic anhydride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 85 percent / pyridine / 0.5 h / 50 °C 2: 46 percent / pyridine; KOH / 1.5 h / 50 °C 3: 54 percent / conc. H2SO4 / acetic acid / 2 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: F3C-SO3H / CH2Cl2 / 0.5 h / Ambient temperature 2: AlCl3 / 0.25 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C 7: 80 percent / H2 / 10percent Pd/C / methanol / 22 h / Ambient temperature | ||
Multi-step reaction with 7 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C 7: 80 percent / H2 / 10percent Pd/C / methanol / 22 h / Ambient temperature | ||
Multi-step reaction with 7 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C 7: 80 percent / H2 / 10percent Pd/C / methanol / 22 h / Ambient temperature |
Multi-step reaction with 7 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C 7: 80 percent / H2 / 10percent Pd/C / methanol / 22 h / Ambient temperature | ||
Multi-step reaction with 7 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C 7: 80 percent / H2 / 10percent Pd/C / methanol / 22 h / Ambient temperature | ||
Multi-step reaction with 7 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C 7: 80 percent / H2 / 10percent Pd/C / methanol / 22 h / Ambient temperature | ||
Multi-step reaction with 7 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C 7: 80 percent / H2 / 10percent Pd/C / methanol / 22 h / Ambient temperature | ||
Multi-step reaction with 7 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C 7: 80 percent / H2 / 10percent Pd/C / methanol / 22 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 42 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 10 percent / tetrahydrofuran / 0.42 h / -50 °C | ||
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 42 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 10 percent / tetrahydrofuran / 0.42 h / -50 °C | ||
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 42 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 10 percent / tetrahydrofuran / 0.42 h / -50 °C |
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 42 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 10 percent / tetrahydrofuran / 0.42 h / -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C | ||
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C | ||
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C |
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C | ||
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C | ||
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C | ||
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C | ||
Multi-step reaction with 6 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C 6: 14 percent / tetrahydrofuran / 0.42 h / -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C | ||
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C | ||
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C |
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C | ||
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C | ||
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C | ||
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 83 percent / LiCl, Et3N / Cl2Pd(PPh3)2 / acetonitrile; H2O / within 30 min to 70 deg C and 1 h, 70 deg C | ||
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 32 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 42 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C | ||
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 42 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C | ||
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 42 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C |
Multi-step reaction with 5 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C 5: 42 percent / Ph3P, Et4NCl, Et3N / Pd(OAc)2, Ph3P / H2O; acetonitrile / 15 min, room t. and 40 min, 50 deg C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature |
Multi-step reaction with 3 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C | ||
Multi-step reaction with 4 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C | ||
Multi-step reaction with 4 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 47 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / hexane / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C |
Multi-step reaction with 4 steps 1: 96 percent / tetrahydrofuran / 0 deg C, 5 min and 65 deg C, 20 min 2: 35 percent / Et3SiH, TFA / CH2Cl2 / 0 deg C and room t., 30 min 3: 70 percent / 65percent HNO3 / acetic acid / 2 h / Ambient temperature 4: 88 percent / 2,4,6-collidine / CH2Cl2 / 0.42 h / -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol 3: pyridine / CH2Cl2 / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol 3: pyridine / CH2Cl2 / 1 h / 20 °C 4: 82 percent / H2, CH3COOH / 5percent Pd/C / 20 °C / 3102.9 Torr | ||
Multi-step reaction with 4 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol 3: pyridine / CH2Cl2 / 1 h / 20 °C 4: 70 percent / CF3COOH / 0.5 h / Heating | ||
Multi-step reaction with 4 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol 3: pyridine / CH2Cl2 / 1 h / 20 °C 4: 13 percent / H2, CH3COOH / 5percent Pd/C / 20 °C / 3102.9 Torr |
Multi-step reaction with 4 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol 3: pyridine / CH2Cl2 / 1 h / 20 °C 4: 93 percent / CH3COOH / 0.5 h / Heating | ||
Multi-step reaction with 4 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol 3: diethyl ether / 1 h / 0 °C 4: 53 percent / NaN3, AlCl3 / tetrahydrofuran / 24 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol 3: pyridine / CH2Cl2 / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol 3: pyridine / CH2Cl2 / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol 3: pyridine / CH2Cl2 / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol | ||
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid 2: hydrogen / palladium on activated charcoal / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 44 percent / conc. HNO3, conc. H2SO4 / -20 °C 2: 60 percent / H2 / 5percent Pd/C / ethanol 3: diethyl ether / 1 h / 0 °C | ||
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid 2: hydrogen / palladium on activated charcoal / ethanol 3: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) NaH; 2.) LDA / 1.) THF; 2.) THF, -78 deg C, 15 min. 2: 90 percent / NaOMe / ethanol / 19 h / Heating 3: 1.) Et3N, CH3SO2Cl; 2.) LiAlH4 / 1.) THF, -23 deg C, 1 h; 2.) ether, room temp., 2 h | ||
Multi-step reaction with 4 steps 1: 1) NaH / 1) THF, 2a) THF, -78 deg C, 15 min, 2b) -78 deg C to RT 2: 90 percent / NaOEt / ethanol / 19 h / Heating 3: NEt3 / tetrahydrofuran / -20 °C 4: LiAlH4 / diethyl ether / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / HNO3 (100percent) / acetic acid / 2.5 h / Ambient temperature 2: 86 percent / H2, conc. HCl / Pd-C(10percent) / H2O / 11 h / raum temp., 40 -> 50 deg C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With dmap In 1,2-dichloro-benzene at 130℃; for 8h; | Compound 172: 1-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-5-ethylphenyl]-ethanone Compound 172: 1-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-5-ethylphenyl]-ethanone; 3-Ethyl-6-hydroxyacetophenone (341 mg), 4-chloro-6,7-dimethoxyquinoline (154 mg), and 4-dimethylaminopyridine (254 mg) were suspended in o-dichlorobenzene (6.5 ml), and the suspension was stirred at 130°C for 8 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-hexane to give the title compound (48 mg, yield 20%). 1H-NMR (CDCl3, 400 MHz): δ 1.21 (t, J = 7.6 Hz, 3H), 2.44 (s, 3H), 2.65 (q, J = 7.6 Hz, 2H), 3.96 (s, 3H), 3.97 (s, 3H), 6.35 (d, J = 5.6 Hz, 1H), 7.00 (d, J = 8.0 Hz, 1H), 7.32 - 7.37 (m, 2H), 7.48 (s, 1H), 7.67 (s, 1H), 8.42 (d, J = 5.6 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 352 (M+1)+ |
20% | With dmap In 1,2-dichloro-benzene at 160℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone; acetonitrile | 77.b 6-Ethyl-4-(N-Ethylsulfonyl-N-Methyl)Amino-2,2-Dimethyl-Chroman b) 6-Ethyl-2,2-dimethyl-4-chromanone is obtained analogously to the procedure indicated in Example 18 b) from 5-ethyl-2-hydroxyacetophenone and acetone in the presence of pyrrolidine in acetonitrile as solvent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With pyrrolidine In toluene for 24h; Heating / reflux; | 105.1 Step 1: 6-Ethyl-2,2-spirocvclopentyl-2.3-dihydrochromen-4-one. A mixture of 2-hydroxyl-5-ethylacetophenone (5.0 g, 30.47 mmol), cyclopentanone (3.30 g, 39.61 mmol), and pyrrolidine (0.54 g, 7.62 mmol) in toluene (70 mL) was heated at reflux with Dean-Stark trap for 24h. The mixture was cooled, washed with 5 N HCl, brine, dried over MgSC>4, concentrated and purified by ISCO (5% EtOAc/Hexanes) to give the title compound as a light yellow oil (5.93 g, 84%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With pyrrolidine for 12h; Heating / reflux; | 128.1 Step 1: 6-ethyl-2,2-spirocvclohexylchroman-4-one. A solution of cyclohexyl ketone (8 ml, 78 mmol), l-(5-ethyl-2- hydroxyphenyl)ethanone (8 g, 48.7 mmol), and pyrrolidine (1.6 ml, 19.5 mmol) were refluxed using a Dean Stark trap for 12 h. The cooled reaction mixture was diluted with 100 ml ether, washed with 30 ml HCl (aq., 5M), dried over MgSC>4 and evaporated. Column chromatography (3% EtOAc in Hexanes) gave 6-ethyl-2,2- spirocyclohexylchroman-4-one as a yellow oil 9.4g (38.5 mmol, 79%). MS m/z: 245 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 3-ethyl-6-hydroxyacetophenone With potassium hydroxide In ethanol for 0.0833333h; Stage #2: 4-bromo-benzaldehyde In ethanol at 20℃; Stage #3: With hydrogenchloride In ethanol; water for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In toluene at 20℃; | tert-Butyl [(R)-2-(2-Acetyl-4-ethylphenoxy)-1-methylethyl]carbamate (2d) ADDP (7.57 g, 30 mmol) was added portionwise at room temperature to a solution of 5d (6.60 g, 30 mmol), tert-butyl [(R)-2-hydroxy-1-methylethyl]carbamate (4.93 g, 30 mmol), and PBu3 (8.24 mL, 33 mmol) in toluene (150 mL). After stirring overnight, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with hexane/AcOEt (5/1) and recrystallized from hexane/AcOEt to give 2d (3.36 g, 35% yield) as colorless prisms. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: 3-ethyl-6-hydroxyacetophenone; 2-chloro-4-nitrobenzoyl chloride With potassium carbonate In acetone for 15h; Reflux; Stage #2: With sulfuric acid; acetic acid for 2h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With trichlorophosphate at 0 - 20℃; | 3 Synthesis of 6-substituted 4-oxo-4H-chromene-3-carbaldehydes General procedure: POCl3 (112.6 g, 0.72 mol) was added slowly to a well stirred and cooled (0-5 °C) mixture of N,N-dimethylformamide (53.6 g, 0.72 mol), o-hydroxyacetophenone c1 (20.1 g, 0.14 mol) for 30 min. The ice bath was removed and the mixture was further stirred for 8-12 h at room temperature. The orange-yellow colored organic mass was poured into crushed ice (400 g) with stirring, extracted with EtOAc (8 * 50 mL) and the layers were separated. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Thus obtained residue was subjected to column chromatography purification on silica gel . |
With trichlorophosphate at 20℃; | ||
With trichlorophosphate at 80℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride In toluene at 110℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: Reflux 2.1: trichloroisocyanuric acid / tetrahydrofuran / 0.5 h / 20 °C 2.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.1% | With potassium hydroxide In ethanol; water at 20℃; for 30h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyrrolidine / acetone; acetonitrile 2: hydroxylamine hydrochloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyrrolidine / acetone; acetonitrile 2: hydroxylamine hydrochloride 3: hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyrrolidine / acetone; acetonitrile 2: hydroxylamine hydrochloride 3: hydrogenchloride 4: triethanolamine / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: pyrrolidine / acetone; acetonitrile 2: hydroxylamine hydrochloride 3: hydrogenchloride 4: triethanolamine / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: pyrrolidine / acetone; acetonitrile 2: hydroxylamine hydrochloride 3: hydrogenchloride 4: triethanolamine / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 3-ethyl-6-hydroxyacetophenone; ethanoate With sodium hydride In tetrahydrofuran; mineral oil for 0.0833333h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In methanol; water at 20℃; for 14h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; | 22 Intermediate 56: 1 -(5-ethyl-2-methoxyphenyl)ethanone To a solution of 1 -(5-ethyl-2-hydroxyphenyl)ethanone (2.33 g, 14.19 mmol) in N,N- Dimethylformamide (15 mL) was added iodomethane (1 .325 mL, 21 .28 mmol). The reaction mixture was stirred at rt for 18 h. Water (10 mL) was added, and then the mixture was extracted with EtOAc (3x20 mL). The combined organic layers were washed with brine (10 mL). The organic layer was dried over Na2S04, and then concentrated under reduced pressure to give the product 1 -(5-ethyl-2-methoxyphenyl)ethanone (2.50 g, 12.81 mmol, 90 % yield) as a yellow oil. m/z: [M + H]+ Calcd for C11 H15O2 179.1 ; Found 179 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With potassium hydroxide In ethanol at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With N-Bromosuccinimide In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 3-ethyl-6-hydroxyacetophenone; oxalic acid diethyl ester With methanol; sodium methylate In 1,4-dioxane at 120℃; for 0.333333h; Microwave irradiation; Stage #2: With hydrogenchloride In 1,4-dioxane at 120℃; for 0.666667h; Microwave irradiation; |
Tags: 24539-92-2 synthesis path| 24539-92-2 SDS| 24539-92-2 COA| 24539-92-2 purity| 24539-92-2 application| 24539-92-2 NMR| 24539-92-2 COA| 24539-92-2 structure
[ 55108-28-6 ]
1,1'-(2-Hydroxy-5-methyl-1,3-phenylene)diethanone
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