[ CAS No. 15832-09-4 ]

Name: 6-Methoxy-3(2H)-benzofuranone
Brand: Ambeed
SKU: A152419
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Structure of 15832-09-4

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Quality Control of [ 15832-09-4 ]

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COA GC NMR CNMR HPLC/UPLC LC-MS

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SDS

Product Details of [ 15832-09-4 ]

CAS No. :	15832-09-4	MDL No. :	MFCD02257681
Formula :	C₉H₈O₃	Boiling Point :	313.0±41.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	BLLMRPOVMOPQKC-UHFFFAOYSA-N
M.W :	164.16	Pubchem ID :	585368
Synonyms :

Computed Properties of [ 15832-09-4 ]

TPSA :Topological Polar Surface Area	35.5	H-Bond Acceptor Count :	3
XLogP3 :	1.4	H-Bond Donor Count :	0
SP3 :	0.22	Rotatable Bond Count :	1

Safety of [ 15832-09-4 ]

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

Application In Synthesis of [ 15832-09-4 ]

Upstream synthesis route of [ 15832-09-4 ]
Downstream synthetic route of [ 15832-09-4 ]

[ 15832-09-4 ] Synthesis Path-Upstream 1~13

1
[ 6272-26-0 ]
[ 74-88-4 ]
[ 15832-09-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6.00 h;	General procedure: To a stirred solution of compound 3 (5 g, 33 mmol) in DMF (20 mL) was added anhydrous potassium carbonate (13.84 g, 100 mmol), iodomethane (3.2 mL, 51 mmol) or 4-methoxybenzyl chloride (5.5 mL, 35 mmol) at 0°C. The reaction mixture was warmed slowly to r.t. and stirred for 6 h. The mixture was poured into water (100 mL) and extracted with ethyl acetate (3 × 100 mL). The combined organic layers were washed with water (2 × 300 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give compounds 5a and 5b.

Reference： [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6360 - 6366
[2] Tetrahedron Asymmetry, 2008, vol. 19, # 7, p. 788 - 795
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3226 - 3230
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4520 - 4523
[5] Patent: WO2005/73224, 2005, A2. Location in patent: Page/Page column 86-87
[6] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 195 - 208

2
[ 52116-39-9 ]
[ 15832-09-4 ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium acetate; acetic anhydride In toluene for 48.00 h; Heating / reflux	Step 3: The 2-(carboxymethoxy)-4-methoxy-benzoic acid compound obtained from the step 2 (11.3 g, 50 mmol) was dissolved in acetic anhydride (100 ml) and anhydrous sodium acetate (10.0 g, excess) was added. The reaction mixture was heated to 150° C. for 4 hrs. During this time the reaction mixture turned dark red. The reaction mixture was cooled to room temperature and quenched carefully with ice cold water. The red solid obtained was filtered and washed well with water. The red solid obtained was suspended in 1 N HCl and refluxed for 2 hrs. A dark red solid, 6-methoxy-benzofuran-3(2H)-one, precipitated from the reaction mixture. It was filtered and washed well with water. It was dried at 40° C. and used for the next step without further purification. Yield: 4.7 g (57percent); (M+H): 165.
57%	Stage #1: at 150℃; for 4.00 h; Stage #2: With hydrogenchloride In water for 2.00 h;	Step 3: The 2- (carboxymethoxy)-4-methoxy-benzoic acid compound obtained from the step 2 (11.3 g, 50 mmol) was dissolved in acetic anhydride (100 ml) and anhydrous sodium acetate (10.0 g, excess) was added. The reaction mixture was heated to 150 C for 4 hrs. During this time the reaction mixture turned dark red. The reaction mixture was cooled to room temperature and quenched carefully with ice cold water. The red solid obtained was filtered and washed well with water. The red solid obtained was suspended in 1 N HC1 and refluxed for 2 hrs. A dark red solid, 6-METHOXY-BENZOFURAN-3 (2H) -one, precipitated from the reaction mixture. It was filtered and washed well with water. It was dried at 40 C and used for the next step without further purification. Yield: 4.7 g (57percent); (M+H): 165.
57%	Stage #1: With sodium acetate In acetic anhydride at 150℃; for 4.00 h; Stage #2: With hydrogenchloride In water for 2.00 h; Heating / reflux	Step 3: The 2-(carboxymethoxy)-4-methoxy-benzoic acid compound obtained from the step 2 (11.3 g, 50 mmol) was dissolved in acetic anhydride (100 ml) and anhydrous sodium acetate (10.0 g, excess) was added. The reaction mixture was heated to 150° C. for 4 hrs. During this time the reaction mixture turned dark red. The reaction mixture was cooled to room temperature and quenched carefully with ice cold water. The red solid obtained was filtered and washed well with water. The red solid obtained was suspended in 1 N HCl and refluxed for 2 hrs. A dark red solid, 6-methoxy-benzofuran-3 (2H)-one precipitated from the reaction mixture. It was filtered and washed well with water. It was dried at 40° C. and used for the next step without further purifications. Yield: 4.7 g (57percent); 165 (M+H).

Reference： [1] Patent: US2009/54454, 2009, A1. Location in patent: Page/Page column 23
[2] Patent: WO2004/99191, 2004, A2. Location in patent: Page 52
[3] Patent: US2005/4162, 2005, A1. Location in patent: Page/Page column 13

3
[ 6272-26-0 ]
[ 77-78-1 ]
[ 15832-09-4 ]

Yield	Reaction Conditions	Operation in experiment
72.84%	With potassium carbonate In acetone at 20℃; for 2.00 h;	To a solution of 1-12 (1.5 g, 10 mmol) in acetone (7 ml) was added K₂CO₃ (2.073 g, 15 mmol), followed by the addition of dimethyl sulfate (1.387 g, 11 mmol). The mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and diluted with water. The aqueous layer was extracted with dichloromethane (3 * 50 ml), dried with Na₂SO₃, and evaporated to dryness to yield 2-12 as yellow solid which was used without further purification, 72.84percent yield. M.p. 116-118 °C (Lit. m.p. 102-103 °C); ¹H NMR (CDCl₃, 500 MHz): δ 7.57 (d, J = 8.6 Hz, H4), 6.65 (dd, J1 = 2 Hz, J2 = 8.6 Hz, H5), 6.55 (d, J = 2 Hz, H7), 4.63 (s, 2H), 3.89 (s, 3H). HRMS (TOF-ES) calcd for C₉H₉O₃⁺ ([M+1]⁺): 165.0552, found 165.0535.

Reference： [1] European Journal of Medicinal Chemistry, 2015, vol. 94, p. 195 - 210
[2] Organic and Biomolecular Chemistry, 2008, vol. 6, # 19, p. 3486 - 3496

4
[ 150-19-6 ]
[ 107-14-2 ]
[ 15832-09-4 ]

Yield	Reaction Conditions	Operation in experiment
54.8%	With hydrogenchloride; sodium hydroxide In 1,4-dioxane; water	EXAMPLE 5 Preparation of 6-methoxy-3-benzofuranone Chloroacetonitrile (3.5 ml, 55.2 mmol) was added dropwise to a stirred solution containing 3-methoxyphenol (5 ml, 46 mmol) and zinc chloride (6.9 g, 50.6 mmol) in anhydrous dioxane (30 ml) at room temperature. The resulting solution was saturated with dry hydrogen chloride gas. After stirring at room temperature overnight, the yellow precipitate was filtered and washed with anhydrous ether (100 ml). The collected precipitate was dissolved in water (80 ml) and heated to reflux for 1 hour. The solution was allowed to cool to approximately 40° C., and aqueous sodium hydroxide (20percent w/v) (7.5 ml) was added. After stirring at that temperature for 30 minutes a pale yellow precipitate had formed. A heterogeneous system was then taken to pH.approx.7 by addition of hydrochloric acid (1 M). The precipitate was filtered, washed with water, and recrystallized from acetone to give the desired compound as a light yellow powder (4.14 g, 54.8percent). ¹H NMR: 8 (ppm): 3.85 (OMe); 4.9 (CH2); 6.50-6.46 (2 H-Phenyl); 7.70-7.66 (1 H-Phenyl).

Reference： [1] Patent: US6307070, 2001, B1

5
[ 77336-36-8 ]
[ 15832-09-4 ]

Reference： [1] Chemistry - An Asian Journal, 2015, vol. 10, # 1, p. 91 - 95

6
[ 60965-24-4 ]
[ 15832-09-4 ]

Reference： [1] Organic Letters, 2009, vol. 11, # 1, p. 17 - 20
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 668 - 672

7
[ 415714-37-3 ]
[ 15832-09-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6354 - 6363
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 824 - 827

8
[ 108-46-3 ]
[ 15832-09-4 ]

Reference： [1] European Journal of Medicinal Chemistry, 2015, vol. 94, p. 195 - 210
[2] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 195 - 208
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3226 - 3230

9
[ 2491-39-6 ]
[ 15832-09-4 ]

Reference： [1] European Journal of Medicinal Chemistry, 2015, vol. 94, p. 195 - 210

10
[ 552-41-0 ]
[ 15832-09-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 668 - 672

11
[ 2088-24-6 ]
[ 15832-09-4 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 2, p. 104 - 106

12
[ 4940-44-7 ]
[ 10035-10-6 ]
[ 15832-09-4 ]

Reference： [1] Proceedings - Indian Academy of Sciences, Section A, 1949, vol. <A> 29, p. 394,401

13
[ 186581-53-3 ]
[ 60-29-7 ]
[ 19202-27-8 ]
[ 15832-09-4 ]

Reference： [1] Journal of the Chemical Society, 1915, vol. 107, p. 1493

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
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H300	Fatal if swallowed
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H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 15832-09-4 ]

Quality Control of [ 15832-09-4 ]

Related Doc. of [ 15832-09-4 ]

Product Details of [ 15832-09-4 ]

Computed Properties of [ 15832-09-4 ]

Safety of [ 15832-09-4 ]

Application In Synthesis of [ 15832-09-4 ]

[ 15832-09-4 ] Synthesis Path-Upstream 1~13

[ 15832-09-4 ] Synthesis Path-Downstream 1~10