[ CAS No. 3588-80-5 ] {[proInfo.proName]}

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Quality Control of [ 3588-80-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 3588-80-5 ]

Product Details of [ 3588-80-5 ]

CAS No. :	3588-80-5	MDL No. :	MFCD00512042
Formula :	C₁₁H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	174.20	Pubchem ID :	-
Synonyms :

Safety of [ 3588-80-5 ]

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Application In Synthesis of [ 3588-80-5 ]

* 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.

Upstream synthesis route of [ 3588-80-5 ]
Downstream synthetic route of [ 3588-80-5 ]

[ 3588-80-5 ] Synthesis Path-Upstream 1~3

1
[ 3588-80-5 ]
[ 77-78-1 ]
[ 10075-63-5 ]

Reference： [1] Journal of the American Chemical Society, 1931, vol. 53, p. 4114,4116

2
[ 83-56-7 ]
[ 77-78-1 ]
[ 3588-80-5 ]
[ 10075-63-5 ]

Reference： [1] Tetrahedron, 1982, vol. 38, # 15, p. 2347 - 2354
[2] Journal of the Chemical Society, 1907, vol. 91, p. 109
[3] Chemische Berichte, 1903, vol. 36, p. 569

3
[ 67-56-1 ]
[ 83-56-7 ]
[ 3588-80-5 ]
[ 10075-63-5 ]

Reference： [1] Australian Journal of Chemistry, 1993, vol. 46, # 5, p. 731 - 737

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate In acetone at 15 - 28℃; Inert atmosphere;	1 Under nitrogen protection,To a 2 L reaction flask, 160.2 g of Compound 1 was added, 1 L of acetone was added, stirring was started, and 165.6 g of potassium carbonate was added.The ice water bath was cooled down to below 15 ° C, and 151.3 g of dimethyl sulfate was added dropwise. The exotherm was obvious, the temperature was controlled below 25 ° C, and the mixture was stirred at 28 ° C overnight.Pour into 3 L of ice water and stir for 0.5 hours.Filter by suction and wash the filter cake (0.5L × 3). The filter cake was dissolved in 2 L of MTBE and washed with saturated sodium chloride (1 L).50 g of anhydrous sodium sulfate was dried and filtered. Concentrate under reduced pressure at 40 ° C to the remaining 1/3 solvent.The temperature was raised to reflux, and 0.5 L of n-heptane was added to cool and crystallize.The product was collected by filtration and dried under vacuum at 40 ° C to give a pale yellow powder, 125.4 g.Yield 72%, 98.9% purity.
64.8%	With sodium hydroxide In water at 20℃; for 0.5h; Inert atmosphere;	5.5-1 5-(1) Intermediate 5-a was synthesized according to Scheme 17 below In a 1 L round-bottom flask reactor, 33 g of sodium hydroxide and 329 mL of water were added at room temperature to make a 2.5 M aqueous solution, and 1,5-dihydroxynaphthalene (50 g, 0.312 mol) was added and dissolved.After bubbling the reaction solution of the reactor with nitrogen, dimethyl sulfate (43.3 g, 0.343 mol) was slowly added dropwise under the same conditions.After completion of the dropwise addition, the mixture was stirred for 30 minutes.When the reaction is over, extract with ethyl acetate and water, discard the organic layer, and add 10M hydrochloric acid to the water layer.Ethyl acetate is added to the precipitated fish and extracted.The organic layer is distilled under pressure.Column chromatography gave intermediate 5-a (35 g, yield 64.8%)
55%	With sodium hydroxide

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: 1,5-dihydroxynaphthalene With potassium carbonate In acetone Stage #2: methyl iodide
44%	Stage #1: 1,5-dihydroxynaphthalene With potassium carbonate In acetone at 20℃; for 3h; Stage #2: methyl iodide at 0 - 20℃; for 12h;	Step-1: 5-Methoxynaphthalen-1-ol To a stirred solution of 1,5-dihydroxy naphthalene (40 g, 0.25 mol) in dry acetone (200 mL) was added, K2CO3 (34.5 g, 0.25 mol) and the mixture was stirred at RT for 3 h, and then cooled to 0° C. To this, a solution of methyl iodide (124.5 mL, 2 mol) in dry acetone (100 mL) was added drop wise and the reaction mixture was stirred for 2 h at 0° C. and then for 10 h at RT. After completion (TLC), the mixture was filtered and washed with EtOAc. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (8% EtOAc:Hexanes) to afford the desired compound (19.2 g, 44%) as a light green solid.
41%	With potassium carbonate In acetone for 27h;	13.1 synthesis of intermediates 55-1 1, 5-die hydroxy-naphthalene (10g, 62mmol) and potassium cyclocarbonate (20g, 144mmol) with the adaptation stirring time after [...] to 3. Then methane mol % of a multifunctional crosslinking agent (8.8g, 62mmol) after blended for filtering pressure sensitive place time was 24. Distilled of decompressing filtrate obtained residue silica gel tube chromatography for purifying 55-1 intermediate that is (5.3g, 41%)is obtained. It is found out that to the resulting compound is LC-MS (C11H10O2 M computed value: 174.07 174.72 measurements)

Yield	Reaction Conditions	Operation in experiment
67%	With potassium carbonate; potassium iodide In acetonitrile for 36h; Heating;

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;	1-[(2-bromo-5-methoxybenzyl)oxy]-5-methoxynaphthalene To a mixture of 5-methoxy-1-naphthol (26.0 g, 149 mmol), triphenylphosphine (43.3 g, 165 mmol), <strong>[150192-39-5](2-bromo-5-methoxyphenyl)methanol</strong> (36.0 g, 166 mmol), and THF (500 ml) was added DEAD (28.7 g in 50 ml THF, 165 mmol) dropwise. The reaction was then stirred overnight, concentrated, dissolved in a minimum amount of ether, and cooled at approx. -30 C. to form awhite precipitate (PPh3O and reduced DEAD) which was filtered off. The filtrate was concentrated and dissolved in a minimum amount of dichloromethane and cooled to -30 C. The precipitate was filtered off on a silica plug and the filtrate was concentrated to 28.7 g (51.5%) of white solid. mp 120-121 C.; 1H NMR (300 MHz, DMSO-d6) delta 3.77 (3H, s), 3.96 (3H, s), 5.26 (2H, s), 6.94 (1H, dd, J=8.8 Hz, 3.1 Hz), 7.01 (1H, d, J=7.6 Hz), 7.11 (1H, d, J=7.6 Hz), 7.28 (1H, d, J=3.1 Hz), 7.42 (2H, m), 7.61 (1H, d, J=8.8 Hz), 7.75 (2H, appd); MS m/z 373/275(Br pattern) (M+H+).

Yield	Reaction Conditions	Operation in experiment
60%	With palladium diacetate; caesium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 140℃; for 24h;	3.17 g (10 mmol) of <strong>[31928-44-6]2-bromo-4-chloro-1-iodobenzene</strong>, 1.92 g (11 mmol) of 5-methoxy-1-naphthol, 0.112 g (0.5 mmol) of palladium acetate, 0.651 g (2.0 mmol) of triphenylphosphine, and 13 g (40 mmol) of cesium carbonate were dissolved in 60 mL of dimethylformamide (DMF), and then stirred at about 140 C. for about 24 hours. The resulting mixture was cooled down to room temperature, and 60 mL of water was added thereto, followed by extraction three times with ethylether. An organic layer was collected and was dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 1.70 g of Intermediate I-1 (Yield: 60%). This compound was identified using liquid chromatography-mass spectroscopy (LC-MS).
58%	With palladium diacetate; caesium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 140℃; for 24h;	3.17 g (10 mmol) of <strong>[31928-44-6]2-bromo-4-chloro-1-iodobenzene</strong>, 1.92 g (11 mmol) of 5-methoxy-1-naphthol, 0.112 g (0.5 mmol) of palladium acetate, 0.651 g (2.0 mmol) of triphenylphosphine, and 13 g (40 mmol) of cesium carbonate were dissolved in 60 mL of DMF, and then the mixture was stirred at a temperature of 140 C. for 24 hours. The reaction solution was cooled to room temperature, and then 60 mL of water was added thereto. Then, an extraction process was performed three times using 60 mL of ethylether. The collected organic layer was dried using magnesium sulfate and the residue obtained by evaporating the solvent was separation-purified by silica gel column chromatography to obtain 1.64 g (yield 58%) of Intermediate I-5.

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23%	With sodium hydroxide In ethanol; water at 20℃; for 2h;
	With potassium hydroxide; water
	With potassium hydroxide at 50 - 60℃;
	With sodium hydroxide In diethyl ether
	With potassium hydroxide at 50℃;
	With potassium hydroxide

41%	Stage #1: 1,5-dihydroxynaphthalene With potassium carbonate In acetone for 3h; Stage #2: methyl iodide In acetone for 24h;	2 Synthesis of intermediate 22-1 1,5-dihydroxy acetone, (10g) and potassium carbonate (20g) diluted to the acetone was stirred for 3 hours. After the addition was then iodo methane (8.8g) and then stirred for 24 hours under reduced pressure and filtered. Separating the residue obtained under reduced pressure, the filtrate was evaporated with silica gel column chromatography to obtain the purified intermediate 22-1 (5.3g, 41%)
41%	Stage #1: 1,5-dihydroxynaphthalene With potassium carbonate In acetone for 3h; Stage #2: methyl iodide In acetone for 24h;	24 Synthesis of Intermediate 209-1 10 g of 1,5-dihydroxynaphthalene and 20 g of potassium carbonate were dissolved in acetone, and then, the mixture was stirred for 3 hours. Then, 8.8 g of iodomethane was dropped thereto and the resultant mixture was stirred for 24 hours and filtered under reduced pressure. The result obtained by distilling filtrate under reduced pressure was separated and purified by silica gel column chromatography to obtain Intermediate 209-1 (5.3 g, 41%).
40%	With potassium carbonate In acetone for 10h; Ambient temperature;
40%	With potassium carbonate In acetone at 0 - 20℃; for 12h;
37%	With potassium carbonate In acetonitrile at 82℃; Inert atmosphere;
	With potassium carbonate In acetone
	Stage #1: 1,5-dihydroxynaphthalene With sodium hydride In tetrahydrofuran; paraffin oil at 0℃; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; paraffin oil at 0 - 20℃; Inert atmosphere;

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[ CAS No. 3588-80-5 ] {[proInfo.proName]}

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[ 3588-80-5 ] Synthesis Path-Upstream 1~3

[ 3588-80-5 ] Synthesis Path-Downstream 1~15

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