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Product Details of [ 7182-38-9 ]

CAS No. :7182-38-9 MDL No. :MFCD18393259
Formula : C9H9ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QRXBKSZGQHXBDO-UHFFFAOYSA-N
M.W : 184.62 Pubchem ID :240358
Synonyms :

Safety of [ 7182-38-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7182-38-9 ]

* 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 [ 7182-38-9 ]

[ 7182-38-9 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 24552-27-0 ]
  • [ 7182-38-9 ]
YieldReaction ConditionsOperation in experiment
62% With aluminium trichloride; nitrobenzene 1) 70 deg C, 3 h, 2) r.t., 24 h;
53% With trifluorormethanesulfonic acid at 20℃; for 4h; 11.2 Step-2: Preparation of 3-chloro-l-(4-hydroxyphenyl)propan-l-one Step-2: Preparation of 3-chloro-l-(4-hydroxyphenyl)propan-l-one [0140] A mixture of phenyl 3-chloropropanoate (1.0 g, 5.41 mmol) and trifluoromethanesulfomc acid (2.4 g, 27.0 mmol) were taken in round bottomed flask and stirred for 4 h. After completion of reaction (monitored by TLC), the mixture was concentrated under vacuum. The residue was diluted with ethyl acetate (100 mL), washed with 20 % sodium bicarbonate solution (20 mL x 3), water (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography (30% ethyl acetate/hexane) to obtain the title compound 3-chloro-l-(4-hydroxyphenyl)propan-l-one (0.53 g, 53 % yield) as a white solid. Calculated (M-H): 183.03; Found (M-H): 183.1.
With aluminium trichloride at 100℃;
  • 2
  • [ 339-43-5 ]
  • [ 7182-38-9 ]
  • [ 94913-28-7 ]
YieldReaction ConditionsOperation in experiment
(i) KOAc, MeOH, (ii) /BRN= 2218915/, EtOH; Multistep reaction;
  • 3
  • [ 625-36-5 ]
  • [ 108-95-2 ]
  • [ 7182-38-9 ]
YieldReaction ConditionsOperation in experiment
7% With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 15h;
7% Stage #1: phenol With aluminum (III) chloride In dichloromethane at 0 - 5℃; for 0.166667h; Stage #2: 2-chloropropionyl chloride In dichloromethane at 5℃; 1 Preparation of 1-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one (MMA-205):
Phenol (3.65 g, 0.039 mol, 1 eq.) was dissolved in CH2Cl2 (20 mL) and cooled to 0° C. AlCl3 (5.5 g, 0.0403 mol, 1.03 eq.) was added in few portions, keeping internal temperature below 5° C. and the reaction mixture was stirred for 10 minutes at the same temperature. The solution of 3-chloropropanoyl chloride (5 g, 0.0397 mol, 1.01 eq.) in CH2Cl2 (10 mL) was added dropwise, keeping internal temperature below 5° C., following by the additional stirring overnight. After the reaction was complete, the reaction mixture was quenched with H2O (30 mL), the layers was separated and the water phase was extracted with CH2Cl2 (2×20 mL). Combined organic layers was washed with H2O (2×10 mL) and brine (2×10 mL), dried over Na2SO4 and evaporated. Obtained crude product was purified by CC to give 3-chloro-1-(4-hydroxyphenyl)propan-1-one as orange oil (0.5 g, 7% yield). (0095) To the precooled to 0° C. solution of 3-chloro-1-(4-hydroxyphenyl)propan-1-one (0.5 g, 0.0027 mol) in dihydropyran (5 mL) catalytical amount of TsOH*H2O was added and the obtained mixture was stirred overnight. Evaporation of the solvent gives the crude product of 3-chloro-1-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)propan-1-one (1 g, 0.0017 mol, about 45% yield), which was used in the next step without purification. (0096) To the solution of 3-chloro-1-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)propan-1-one (crude 1 g, 0.0017 mol) in CH2Cl2 (10 mL) at 0° C. the solution of TEA (1 g, 0.01 mol, 4-5eq.) in CH2Cl2 (10 mL) was added in a dropwise manner, following by additional stirring overnight. Evaporation of the solvent and purification of the obtained crude residue results in the target compound (MMA-205) (120 mg, 0.5 mmol, 25% yield); 1H NMR (500 MHz, Chloroform-d) δ 7.95 (d, J=8.7 Hz, 2H), 7.17 (dd, J=17.1, 10.6 Hz, 1H), 7.12 (d, J=8.7 Hz, 1H), 6.43 (d, J=17.0 Hz, 1H), 5.88 (d, J=10.5 Hz, 1H), 5.53 (s, 1H), 3.91-3.80 (m, 1H), 3.66-3.59 (m, 1H), 2.07-1.95 (m, 1H), 1.90 (dd, J=7.1, 3.5 Hz, 2H), 1.80-1.47 (m, 3H); 13C NMR (126 MHz, Chloroform-d) δ 189.4 (s), 161.1 (s), 132.2 (s), 130.9 (s, J=7.1 Hz), 129.3 (s), 116.1 (s), 96.1 (s), 62.1 (s), 30.1 (s), 25.1 (s), 18.5 (s); LC-MS (ESI), RT=3.061 min, m/z 149.2 [M -C5H9O +H]+; HRMS (ESI), RT=1.085 min, m/z 149.06174 [M -C5H9O +H]+, formula C9H8O2.
With aluminium trichloride In carbon disulfide
  • 4
  • [ 7182-38-9 ]
  • [ 53170-93-7 ]
YieldReaction ConditionsOperation in experiment
64% With sodium hydrogencarbonate In water; acetonitrile for 12h; Heating;
YieldReaction ConditionsOperation in experiment
Anisol, β-Chlor-propionylchlorid, AlCl3, CS2;
  • 6
  • [ 7182-38-9 ]
  • [ 53170-92-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 64 percent / NaHCO3 / acetonitrile; H2O / 12 h / Heating 2: 16 percent / diisopropyl ether / 8 h / 50 °C / lactase from Kluyveromyces lactis, KH2PO4 buffer (pH = 6.5)
  • 7
  • [ 108-95-2 ]
  • [ 7182-38-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 60 percent / pyridine / CH2Cl2 / 12 h / Ambient temperature 2: 62 percent / AlCl3, PhNO2 / 1) 70 deg C, 3 h, 2) r.t., 24 h
  • 8
  • [ 341527-03-5 ]
  • [ 7182-38-9 ]
  • 4-{2-[4-(2-Benzyloxyethoxy)phenyl]-1-(2-chloroethyl)-2-phenylvinyl}phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.a a) a) 4-{2-[4-(2-Benzyloxyethoxy)phenyl]-1-(2-chloroethyl)-2-phenylvinyl}phenol is prepared according to the method of example 6b using [(4-benzyloxyethoxy)phenyl]phenylmethanone and 3-chloro-1-(4-hydroxyphenyl)propan-1-one as starting materials. The product is mixture of Z- and E-isomers. 1H NMR (CDCl3): 2.88 and 2.93 (2t, 2H), 3.42 and 3.43 (2t, 2H), 3.74 and 3.84 (2dist.t, 2H), 4.01 and 4.16 (2dist.t, 2H), 4.58 and 4.65 (2s, 2H), 6.55-7.40 (m, 18H).
  • 9
  • [ 937-41-7 ]
  • [ 95605-38-2 ]
  • [ 7182-38-9 ]
YieldReaction ConditionsOperation in experiment
64% With aluminum (III) chloride
  • 10
  • [ 108-95-2 ]
  • [ 7182-38-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 16 h / 100 °C 2: trifluorormethanesulfonic acid / 4 h / 20 °C
  • 11
  • [ 7182-38-9 ]
  • 5-phenyloctahydrocyclopenta[c]pyrrol-5-ol [ No CAS ]
  • 3-(5-hydroxy-5-phenylhexahydrocyclopenta[c]pyrrol-2(1H)-yl)-1-(4-hydroxyphenyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; 11.3 Step-3: Preparation of 3-(5-hydroxy-5-phenylhexahydrocyclopenta[c]pyrrol-2(lH)-yl)-l- (4-hydroxyphenyl)propan-l-one Step-3: Preparation of 3-(5-hydroxy-5-phenylhexahydrocyclopenta[c]pyrrol-2(lH)-yl)-l- (4-hydroxyphenyl)propan-l-one [0141] To a stirred solution of 5-phenyloctahydrocyclopenta[c]pyrrol-5-ol (0.2 g, 0.98 mmol) in dimethylformamide (10 mL) was added potassium carbonate (0.34 g, 2.46 mmol) and 3-chloro-l-(4-hydroxyphenyl)propan-l-one (0.19 g, 1.08 mmol) at room temperature. The reaction mixture was stirred at room temperature for 4 h. After completion of reaction (monitored by TLC), the reaction mixture was diluted with cold water (25 mL) and extracted with ethylacetate (50 mL x 3). The combined organic layer was washed with cold water (15 mL x 3), brine (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude compound which was purified by silica gel column chromatography (5% methanol/dichloromethane) to obtain the title compound 3-(5-hydroxy-5-phenylhexahydrocyclopenta[c]pyrrol-2(lH)-yl)-l-(4- hydroxyphenyl)propan-l-one (0.15 g, 44% yield) as a white solid. Calculated (M+H): 352.18; Found (M+H): 352.3.
  • 12
  • [ 7182-38-9 ]
  • 5-phenyloctahydrocyclopenta[c]pyrrol-5-ol [ No CAS ]
  • 2-(3-hydroxy-3-(4-hydroxyphenyl)propyl)-5-phenyloctahydrocyclopenta[c]pyrrol-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C 2: lithium borohydride / tetrahydrofuran / 4 h / 20 °C
  • 13
  • [ 7182-38-9 ]
  • 4-(4-methoxyphenyl)-5-acetyl-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione [ No CAS ]
  • 4-(4-hydroxyphenyl)-6-(4-methoxyphenyl)-7-acetyl-8-phenyl-2H,6H-pyrimido[2,1-b][1,3]thiazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58.5% With sodium acetate In acetic acid Reflux; 15 Embodiment 15 4 - (4 - hydroxy phenyl) -6 - (4 - methoxyphenyl) -7 - acetyl -8 - phenyl - 2H, 6H - pyrimido [2,1 - b] [1, 3] thiazine (L9) preparation The 4 - (4 - methoxyphenyl) -5 - acetyl -6 - phenyl - 3, 4 - dihydro pyrimidine -2 (1H) - thione 3.38g (10mmol), 3 - chloro -1 - (4 - hydroxy phenyl) -1 - acetone 1.98g (10mmol), sodium acetate/glacial acetic acid (2g/20 ml), heating reflux reaction 8 - 24 hours, TLC monitoring reaction. After cooling, filtering, anhydrous ethanol to recrystallize, shall 2.74g white powder, yield 58.5%.
  • 14
  • [ 7182-38-9 ]
  • 4-(4-chlorophenyl)-5-acetyl-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione [ No CAS ]
  • 4-(4-hydroxyphenyl)-6-(4-chlorophenyl)-7-acetyl-8-phenyl-2H,6H-pyrimido[2,1-b][1,3]thiazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With sodium acetate In acetic acid for 24h; Reflux; 13 Embodiment 13 4 - (4 - hydroxy phenyl) -6 - (4 - chlorophenyl) -7 - acetyl -8 - phenyl - 2H, 6H - pyrimido [2,1 - b] [1, 3] thiazine (L7) preparation The 4 - (4 - chlorophenyl) -5 - acetyl -6 - phenyl - 3, 4 - dihydro pyrimidine -2 (1H) - thione 3.42g (10mmol), 3 - chloro -1 - (4 - hydroxy phenyl) -1 - acetone 1.98g (10mmol), sodium acetate/glacial acetic acid (2g/20 ml), heating reflux reaction 24 hours, TLC monitoring reaction. After cooling, filtering, anhydrous ethanol to recrystallize, shall 2.88g white powder, yield 61.0%.
  • 15
  • [ 7182-38-9 ]
  • 4-(4-hydroxyphenyl)-5-acetyl-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione [ No CAS ]
  • 4-(4-hydroxyphenyl)-6-(4-hydroxyphenyl)-7-acetyl-8-phenyl-2H,6H-pyrimido[2,1-b][1,3]thiazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.2% With sodium acetate In acetic acid Reflux; 14 Embodiment 14 4 - (4 - hydroxy phenyl) -6 - (4 - hydroxy phenyl) -7 - acetyl -8 - phenyl - 2H, 6H - pyrimido [2,1 - b] [1, 3] thiazine (L8) preparation The 4 - (4 - hydroxy phenyl) -5 - acetyl -6 - phenyl - 3, 4 - dihydro pyrimidine -2 (1H) - thione 3.24g (10mmol), 3 - chloro -1 - (4 - hydroxy phenyl) -1 - acetone 1.98g (10mmol), sodium acetate/glacial acetic acid (2g/20 ml), heating reflux reaction 8 - 24 hours, TLC monitoring reaction. After cooling, filtering, anhydrous ethanol to recrystallize, shall 2.96g white powder, yield 65.2%.
  • 16
  • [ 7182-38-9 ]
  • 3-(4-fluorophenyl)-4-[4-[(4-methoxybenzyl)oxy]phenyl]-1H-pyrrol-2,5-dione [ No CAS ]
  • C33H26FNO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrabutylammomium bromide; potassium carbonate In acetonitrile Reflux;
  • 17
  • [ 7182-38-9 ]
  • 3-(4-fluorophenyl)-1-[(3S)-3-hydroxy-3-(4-hydroxyphenyl)propyl]-4-(4-hydroxyphenyl)-1H-pyrrole-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; tetrabutylammomium bromide / acetonitrile / Reflux 2: trifluoroacetic acid / dichloromethane / 1 h / 0 °C 3: dimethylsulfide borane complex; N-(cyclohexyl)benzothiazole-2-sulfenamide / tetrahydrofuran; dichloromethane / 6 h / 0 °C
  • 18
  • [ 7182-38-9 ]
  • C25H18FNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrabutylammomium bromide / acetonitrile / Reflux 2: trifluoroacetic acid / dichloromethane / 1 h / 0 °C
  • 19
  • [ 7182-38-9 ]
  • [ 1474048-79-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / water / 0 °C 2: triethylamine / dichloromethane / 0 °C
  • 20
  • [ 110-87-2 ]
  • [ 7182-38-9 ]
  • 3‐chloro‐1‐(4‐((tetrahydro‐2H‐pyran‐2‐yl)oxy)phenyl)propan‐1‐one [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With toluene-4-sulfonic acid In water at 0℃;
With toluene-4-sulfonic acid at 0℃; 1 Preparation of 1-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one (MMA-205): Phenol (3.65 g, 0.039 mol, 1 eq.) was dissolved in CH2Cl2 (20 mL) and cooled to 0° C. AlCl3 (5.5 g, 0.0403 mol, 1.03 eq.) was added in few portions, keeping internal temperature below 5° C. and the reaction mixture was stirred for 10 minutes at the same temperature. The solution of 3-chloropropanoyl chloride (5 g, 0.0397 mol, 1.01 eq.) in CH2Cl2 (10 mL) was added dropwise, keeping internal temperature below 5° C., following by the additional stirring overnight. After the reaction was complete, the reaction mixture was quenched with H2O (30 mL), the layers was separated and the water phase was extracted with CH2Cl2 (2×20 mL). Combined organic layers was washed with H2O (2×10 mL) and brine (2×10 mL), dried over Na2SO4 and evaporated. Obtained crude product was purified by CC to give 3-chloro-1-(4-hydroxyphenyl)propan-1-one as orange oil (0.5 g, 7% yield). (0095) To the precooled to 0° C. solution of 3-chloro-1-(4-hydroxyphenyl)propan-1-one (0.5 g, 0.0027 mol) in dihydropyran (5 mL) catalytical amount of TsOH*H2O was added and the obtained mixture was stirred overnight. Evaporation of the solvent gives the crude product of 3-chloro-1-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)propan-1-one (1 g, 0.0017 mol, about 45% yield), which was used in the next step without purification. (0096) To the solution of 3-chloro-1-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)propan-1-one (crude 1 g, 0.0017 mol) in CH2Cl2 (10 mL) at 0° C. the solution of TEA (1 g, 0.01 mol, 4-5eq.) in CH2Cl2 (10 mL) was added in a dropwise manner, following by additional stirring overnight. Evaporation of the solvent and purification of the obtained crude residue results in the target compound (MMA-205) (120 mg, 0.5 mmol, 25% yield); 1H NMR (500 MHz, Chloroform-d) δ 7.95 (d, J=8.7 Hz, 2H), 7.17 (dd, J=17.1, 10.6 Hz, 1H), 7.12 (d, J=8.7 Hz, 1H), 6.43 (d, J=17.0 Hz, 1H), 5.88 (d, J=10.5 Hz, 1H), 5.53 (s, 1H), 3.91-3.80 (m, 1H), 3.66-3.59 (m, 1H), 2.07-1.95 (m, 1H), 1.90 (dd, J=7.1, 3.5 Hz, 2H), 1.80-1.47 (m, 3H); 13C NMR (126 MHz, Chloroform-d) δ 189.4 (s), 161.1 (s), 132.2 (s), 130.9 (s, J=7.1 Hz), 129.3 (s), 116.1 (s), 96.1 (s), 62.1 (s), 30.1 (s), 25.1 (s), 18.5 (s); LC-MS (ESI), RT=3.061 min, m/z 149.2 [M -C5H9O +H]+; HRMS (ESI), RT=1.085 min, m/z 149.06174 [M -C5H9O +H]+, formula C9H8O2.
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