[ CAS No. 20426-80-6 ]

Name: 20426-80-6|Chroman-4-carboxylic acid|95%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 20426-80-6 ]

CAS No. :	20426-80-6	MDL No. :	MFCD11848749
Formula :	C₁₀H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	178.18 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 20426-80-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:	N/A
Hazard Statements:	H302-H312-H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 20426-80-6 ]

* 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 [ 20426-80-6 ]

[ 20426-80-6 ] Synthesis Path-Downstream 1~31

1
[ 20426-80-6 ]
[ 64-17-5 ]
[ 112605-35-3 ]

Reference： [1]Journal of Pharmaceutical Sciences,1987,vol. 76,p. 848 - 850

2
[ 491-37-2 ]
[ 7677-24-9 ]
[ 20426-80-6 ]

Reference： [1]Journal of Pharmaceutical Sciences,1987,vol. 76,p. 848 - 850

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[ 113967-29-6 ]
[ 20426-80-6 ]

Yield	Reaction Conditions	Operation in experiment
93.4%	With lithium hydroxide;	d) (R,S)-Chroman-4-carboxylic acid (80d) Compound 80c (1.21 g, 6.3 mmol) was hydrolyzed with lithium hydroxide (1.35 g, 32 mmol) to give the title acid (1.05 g, 93.4%). 1H NMR (300 MHz, CDCl3) δ: 12.66 (s, 1H), 7.20-7.13 (m, 2H), 6.87-6.78 (m, 2H), 4.18 (m, 2H), 3.75 (t, 1H), 2.16-2.03 (m, 2H).

Reference： [1]Patent: US2005/54630,2005,A1 .Location in patent: Page/Page column 46
[2]Synthesis,1987,p. 806 - 809

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[ 74187-63-6 ]
[ 20426-80-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrogenchloride; water; acetic acid; tin(ll) chloride; at 140℃; for 20h;	4-(Trimethylsilyloxy)chroman-4-carbonitrile (7.2 g, 0.029 moles) and tin (II) chloride (23.6 g, 0.125 moles) were dissolved in glacial AcOH (30 mL) and con. HCl (30 mL). The resultant mixture was heated at 140 0C for 20 hours and then cooled to room temp. Diluted the mixture with water (150 mL), extracted with CH2Cl2 (3 x 150 mL), washed the combined extracts with brine and dried (MgSO4). The dried extract was filtered and concentrated under vacuo to afford the title compound as off-white solid (4.45 g. 87% yield). 1H NMR (400 MHz, CDCl3) 7.26 (IH, m), 7.16 (IH, m), 6.84 (IH, m), 4.25 (2H, m), 3.81 (IH, m), 2.32 (IH, m), 2.13 (IH, m).
37%	With hydrogenchloride; tin(II) chloride dihdyrate; acetic acid; In water; at 115℃; for 72h;Inert atmosphere;	Into a 100-mL round-bottom flask, was placed 4-[(trimethylsilyl)oxy]-3,4-dihydro-2H-l- benzopyran-4-carbonitrile (1.5 g, 6.06 mmol, 1.00 equiv), SnCl2.2H20 (5.5 g, 24.37 mmol, 4.00 equiv), AcOH (10 mL), con. HC1 (10 mL). The resulting solution was stirred for 3 days at 115 C. The resulting solution was cooled to 18 C and diluted with water (50 mL). The resulting solution was extracted with ethyl acetate (100 mL x 2). The organic layers combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1/2). The collected fraction was concentrated to give 400 mg (37%) of chroman-4- carboxylic acid as a yellow solid. MS (ES, m/z) [M+H]+: 179.
3.18 g	With hydrogenchloride; acetic acid; tin(ll) chloride; for 40h;Reflux;	A mixture of Example 29A (4.75 g, 19.2 mmol) and SnCh (10.92 g, 57.6 mmol) in HC1 (37%), 20 mL) and AcOH (20 mL) was heated at reflux for 40 h. The residue was concentrated to remove AcOH and then partitioned between CH2C12 and brine. The organic layer was further washed with brine, dried (Na2S04) and concentrated. Chromatography (Si02, 0 - 40% ethyl acetate in hexane) gave the target compound (3.18 g, 93%) as a white solid.

1.2 g

With hydrogenchloride; tin(II) chloride dihdyrate; acetic acid; In water; at 80℃; for 24h;

B. To a solution of 4-((trimethylsilyl)oxy)chroman-4-carbonitrile (1.9 g, 7.68 mmol) in HCl (5.0 mL) and AcOH (5.0 mL) was added SnCl2.(H2O)2 (4.32 g, 19.2 mmol). The reaction was stirred at 80 C for 24 h. water (40 mL) was added to the reaction vessel the org/aq phase was extracted with DCM (3 x 150 mL) . The combined organics were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resulting oil was purified by flash column chromatography with isocratic evolution of EtOAc (40%) and hex (60%) to provide chroman-4-carboxylic acid (1.2 g, 6.7 mmol) as a yellow oil.

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 346 - 357
[2]Patent: WO2006/122200,2006,A1 .Location in patent: Page/Page column 52
[3]Synthetic Communications,1982,vol. 12,p. 763 - 770
[4]Patent: WO2017/123518,2017,A1 .Location in patent: Paragraph 096
[5]Patent: WO2017/143011,2017,A1 .Location in patent: Paragraph 0329-0331
[6]Patent: WO2018/26371,2018,A1 .Location in patent: Paragraph 0302

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[ 33313-82-5 ]