[ CAS No. 487-70-7 ] {[proInfo.proName]}

Name: 487-70-7|2,4,6-Trihydroxybenzaldehyde|95%
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Quality Control of [ 487-70-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 487-70-7 ]

SDS Specification

Alternatived Products of [ 487-70-7 ]

Product Details of [ 487-70-7 ]

CAS No. :	487-70-7	MDL No. :
Formula :	C₇H₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BTQAJGSMXCDDAJ-UHFFFAOYSA-N
M.W :	154.12	Pubchem ID :	68099
Synonyms :

Calculated chemistry of [ 487-70-7 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	37.9
TPSA :	77.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.88
Log Po/w (XLOGP3) :	0.87
Log Po/w (WLOGP) :	0.62
Log Po/w (MLOGP) :	-0.41
Log Po/w (SILICOS-IT) :	0.55
Consensus Log Po/w :	0.5

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.68
Solubility :	3.21 mg/ml ; 0.0208 mol/l
Class :	Very soluble
Log S (Ali) :	-2.09
Solubility :	1.26 mg/ml ; 0.00819 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.6
Solubility :	38.3 mg/ml ; 0.248 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 487-70-7 ]

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

Application In Synthesis of [ 487-70-7 ]

* 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 [ 487-70-7 ]
Downstream synthetic route of [ 487-70-7 ]

[ 487-70-7 ] Synthesis Path-Upstream 1~18

1
[ 487-70-7 ]
[ 2732-18-5 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 373
[2] Tetrahedron Letters, 2009, vol. 50, # 33, p. 4769 - 4772

2
[ 487-70-7 ]
[ 2632-13-5 ]
[ 491-80-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: With thiamine hydrochloride In ethanol at 20℃; for 0.25 h; Green chemistry Stage #2: at 20℃; for 2 h; Green chemistry	General procedure: To prepare catalyst, 0.21 g of thiamine hydrochloride (0.6 mmol) was dissolved in 0.64 mL of water and added 2.4 mLof 95percent ethanol (water : 95percent ethanol = ~1:4). The solution was cooled in an ice bath, then added 0.40 mL of 3 M NaOH(1.2 mmol) dropwise with stirring in a manner such that thetemperature remained below 20 °C. Intense yellow coloured solution changed to pale yellow solution of thiamine (thiazolium ion)/N-heterocyclic carbene (Scheme 1).⁴⁷ In a 25-mL round bottom flask, a mixture of phenacylbromide 1 (2.5 mmol, 0.5 g in case of 1a) and thiamine (0.6 mmol, 25 mol percent) in ethanol (4 mL) was stirred at room temperature for 15 min. Then, salicylaldehyde 2 (2.5 mmol, 0.26 mL in case of 2a) was added slowly and the mixture was stirred at room temperature until the reaction was completed (as monitored by TLC) (Table 3) . The reaction mixture was then poured into 20 mL of distilled water and extracted with ethyl acetate (3 × 10 mL). The organic layer was dried over anhydrous Na₂SO₄ and the solvent was removed under reduced pressure. The resulting product isoflavone 3 was further purified either by recrystallizationor by column chromatography (Ethyl acetate:Hexane, 1:4v/v). All compounds were characterized by their mp and ¹HNMR, ¹³CNMR and mass spectral data.

Reference： [1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1070 - 1076

3
[ 108-73-6 ]
[ 68-12-2 ]
[ 487-70-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With trichlorophosphate In ethyl acetate at 0 - 20℃; for 2 h; Inert atmosphere	To a solution of 15 (1.9 g, 15 mmol) in EtOAc (20 ml) was added DMF (1.26 ml, 16.5 mmol) and POCl₃ (1.5 ml, 16.5 mmol) at 0 °C in an ice bath. Remove ice bath and the solution was stirred for 2 h. Water was added and the reaction mixture was refluxed for 30 min. When the solution cooled down, ethyl acetate was added to extract. The organic layers were combined and washed with brine, and dried over anhydrous Na₂SO₄. And then filtration and concentration in vacuo gave a residue, which was purified by flash column chromatography on silica gel (petroleum ether-EtOAc, 4:1) to yield 16 (2.12 g, 92percent) as a white solid. ¹H NMR (500 MHz, DMSO) δ 9.92 (s, 1H), 5.78 (s, 2H). ¹³CNMR (126 MHz, DMSO) δ 191.4, 167.6, 164.5, 105.0, 94.6.
83%	With trichlorophosphate In water; ethyl acetate	Example 1 - Synthesis of Phloroglucinaldehyde (III) 9 l (1.47 kg, 96.4 moles) of phosphorus oxychloride are added to a solution containing 11.2 kg (88.9 moles) of anhydrous phloroglucinol (II) and 7.5 l (7 kg, 96.4 moles) of N,N-dimethylformamide in 33 l of ethyl acetate. The precipitated solid is filtered and the residue is dissolved in hot water. After cooling to room temperature, the crystallizate is filtered. 11.4 kg of III are obtained (yield: 83percent) having a m.p. of 185°-186°C, E
80%	at 20℃; for 4 h; Inert atmosphere; Cooling with ice	A 100 mL round bottom flask was charged with phloroglucin (3 g, 24 mmol) and DMF (30 mL). After the flask was flushed with Ar and covered with the rubber plug, POCl₃ (2.2 mL, 24 mmol) was added dropwise under the condition of ice bath. After completion of adding, the mixture was stirred at room temperature for 4 h. TLC analysis indicated that the reaction was completed. After quenching the reaction mixture with ice cold water (50 mL), the slurry was extracted with CH₂Cl₂ (20 mL * 3). The combined organic extracts were washed with 20percent LiCl aqueous solution (10 mL * 2), brine and then dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 2:1) to provide 2,4,6-trihydroxybenzaldehyde (2.9 g, 80percent) as a white solid. ¹H NMR (300 MHz, DMSO-d₆) δ 11.46 (s, 2H), 10.65 (s, 1H), 9.93 (s, 1H), 5.79 (s, 2H). ¹³C NMR (75 MHz, DMSO-d₆) δ 190.9, 167.2, 164.1, 104.6, 94.2. MS (ESI): m/z 153.0 [M-H]^-.

70%

With trichlorophosphate In ethyl acetate at 0 - 20℃; for 7 h; Inert atmosphere

To a cooled (0 °C) solution of phloroglucinol (13) (20.0 g, 0.159 mol) and DMF (12.2 mL, 0.159 mol) in EtOAc (300 mL), POCl₃ (14.83 mL, 0.159 mol) was added dropwise within 60 min.
After complete addition the resulting suspension was left to stir at room temperature for 6 h.
When full consumption was achieved, the yellow suspension was poured on ice-water (500 mL), and the two-phase mixture was stirred vigorously while adding satd.
NaOAc solution to it until a pH of 5-6 was reached.
During the addition the solution became dark-red, then it was extracted with EtOAc (4*600 mL).
The combined organic layers were washed with satd. NaCl solution (1*500 mL), dried over Na₂SO₄, filtered, and evaporated to dryness.
The residue was recrystallized from water (200 mL) to provide benzaldehyde 26 (17.18 g, 70percent) as red crystals. ¹H NMR (400 MHz, DMSO-d₆): δ=5.78 (s, 2H, 3-H), 9.92 (s, 1H, CHO), 10.64 (s, 1H, OH), 11.45 (s, 2H, OH); ¹³C NMR (100 MHz, DMSO-d₆): δ=94.1 (C-3), 104.5 (C-1), 164.1 (C-2), 167.2 (C-4), 190.9 (CHO).

Reference： [1] Organic Letters, 2015, vol. 17, # 16, p. 4110 - 4113
[2] Tetrahedron Letters, 2016, vol. 57, # 17, p. 1856 - 1859
[3] Synthetic Communications, 1998, vol. 28, # 15, p. 2861 - 2869
[4] Organic Letters, 2010, vol. 12, # 8, p. 1676 - 1679
[5] Synlett, 2007, # 1, p. 129 - 130
[6] Patent: EP348121, 1989, A1,
[7] Molecules, 2018, vol. 23, # 12,
[8] Bioorganic and Medicinal Chemistry, 2019, vol. 27, # 1, p. 116 - 124
[9] Australian Journal of Chemistry, 2005, vol. 58, # 7, p. 551 - 555
[10] Tetrahedron, 2015, vol. 71, # 52, p. 9662 - 9666
[11] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 19, p. 3151 - 3153
[12] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 6, p. 1750 - 1760

4
[ 6099-90-7 ]
[ 68-12-2 ]
[ 487-70-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With trichlorophosphate In ethyl acetate at 20℃; for 1 h; Cooling with ice	In a 1 L single-necked flask, phloroglucinol dihydrate (38.6 g, 0.238 mol), DMF (55.03 mL, 0.714 mol), ethyl acetate (450 mL),Phosphorus oxychloride (66.32 mL, 0.714 mol) was slowly added dropwise under ice bath.After the addition, transfer to room temperature for 1 h, filter, wash with ethyl acetate, place the filter cake in a 500 mL single-necked flask, add water (150 mL), protect with nitrogen, warm to reflux and maintain for 10 min, then cool to room temperature and then refrigerate in the refrigerator. 1h,Filter, wash with water, collect the filter cake and dry in vacuo without further purification.A white solid was obtained in 36 g, yield 98percent.

Reference： [1] Patent: CN108947787, 2018, A, . Location in patent: Paragraph 0016

5
[ 108-73-6 ]
[ 506-68-3 ]
[ 487-70-7 ]

Reference： [1] Journal of the American Chemical Society, 1929, vol. 51, p. 1269
[2] Helvetica Chimica Acta, 1919, vol. 2, p. 92

6
[ 108-73-6 ]
[ 67-66-3 ]
[ 487-70-7 ]

Reference： [1] Organic Mass Spectrometry, 1984, vol. 19, # 7, p. 330 - 333

7
[ 108-73-6 ]
[ 74-90-8 ]
[ 487-70-7 ]

Reference： [1] Journal of the Chemical Society, 1925, vol. 127, p. 1134
[2] Journal fuer Praktische Chemie (Leipzig), 1922, vol. <2> 104, p. 315,322
[3] Chemische Berichte, 1899, vol. 32, p. 279

8
[ 18470-06-9 ]
[ 530-57-4 ]
[ 487-70-7 ]
[ 109717-92-2 ]

Reference： [1] Food Chemistry, 2016, vol. 199, p. 902 - 910

9
[ 108-73-6 ]
[ 487-70-7 ]

Reference： [1] Chemische Berichte, 1901, vol. 34, p. 1443

10
[ 528-58-5 ]
[ 99-50-3 ]
[ 83-30-7 ]
[ 487-70-7 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 36, p. 18939 - 18944

11
[ 108-73-6 ]
[ 103-70-8 ]
[ 487-70-7 ]

Reference： [1] Journal of the Chemical Society, 1924, vol. 125, p. 195[2] Journal of the Chemical Society, 1925, vol. 127, p. 1132 Anm.

12
[ 491-70-3 ]
[ 99-50-3 ]
[ 487-70-7 ]
[ 30048-34-1 ]
[ 18003-33-3 ]

Reference： [1] Monatshefte fur Chemie, 2016, vol. 147, # 8, p. 1375 - 1383

13
[ 6906-38-3 ]
[ 149-91-7 ]
[ 487-70-7 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 12, p. 5271 - 5278

14
[ 7084-24-4 ]
[ 99-50-3 ]
[ 487-70-7 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 12, p. 5271 - 5278

15
[ 548-83-4 ]
[ 487-70-7 ]
[ 65-85-0 ]

Reference： [1] Tetrahedron, 1994, vol. 50, # 31, p. 9303 - 9314

16
[ 520-18-3 ]
[ 487-70-7 ]
[ 99-96-7 ]

Reference： [1] Tetrahedron, 1994, vol. 50, # 31, p. 9303 - 9314

17
[ 117-39-5 ]
[ 99-50-3 ]
[ 487-70-7 ]

Reference： [1] Tetrahedron, 1994, vol. 50, # 31, p. 9303 - 9314

18
[ 108-73-6 ]
[ 2032-76-0 ]
[ 487-70-7 ]

Reference： [1] Chemische Berichte, 1964, vol. 97, p. 2606 - 2613

[ 487-70-7 ] Synthesis Path-Downstream 1~67

1
[ 108-73-6 ]
[ 487-70-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With trichlorophosphate; In N,N-dimethyl-formamide; at 0 - 20℃; for 4h;Inert atmosphere;	Under Ar atmosphere, phloroglucinol (3g, 0.024mol) was dissolved in anhydrous DMF (30mL),phosphorus oxychloride(2.2 mL, 0.024 mol) was slowly added dropwise at 0 C. After the addition, the temperature was raised to room temperature and stirred for 4 hours.After the reaction, the reaction solution was poured into ice to quench it.It was extracted with a mixed solvent (dichloromethane: methanol = 10: 1), concentrated, and then dissolved with ethyl acetate.Subsequently, the remaining DMF was repeatedly washed with saturated saline and 20% LiCl solution, and the solvent was evaporated to dryness under reduced pressure.After flash column chromatography (petroleum ether: ethyl acetate = 2: 1),Compound 1-1 (white solid, 2.9 g) was obtained in a yield of 80%.

Reference： [1]Patent: CN110272436,2019,A .Location in patent: Paragraph 0093-0096
[2]Chemische Berichte,1901,vol. 34,p. 1443

2
[ 487-70-7 ]
[ 88-03-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogenchloride; zinc; In diethyl ether; ethyl acetate; for 0.166667h;Cooling with ice;	In a 500 mL single-necked flask, intermediate 1 (10 g, 0.065 mol), ethyl acetate (25 mL), diethyl ether (25 mL), zinc powder (12.73 g, 0.194 mol),In an ice bath, concentrated hydrochloric acid (33 mL) was slowly added dropwise with vigorous stirring. After the addition was completed, the reaction was continued for 10 min. The zinc powder was removed by filtration, water was added, ethyl acetate was extracted, washed with water, and brine was evaporated.Further purification was carried out to obtain 9 g of a white solid, yield 99%.
99%	With hydrogenchloride; zinc; In diethyl ether; water; ethyl acetate; for 0.166667h;Cooling with ice;	In a 500 mL single-necked flask, intermediate 4 (10 g, 0.065 mol), ethyl acetate (25 mL), diethyl ether (25 mL), zinc powder (12.73 g, 0.194 mol), ice bath, vigorously stirred Concentrated hydrochloric acid (33 mL) was added dropwise, and the reaction was continued for 10 min. The zinc powder was removed by filtration, water was added, ethyl acetate was evaporated, washed with water, brine, and evaporated.A white solid 9 g was obtained in a yield of 99%.
78%	With hydrogenchloride; methyl orange; sodium cyanoborohydride; In tetrahydrofuran; water; at 20℃; for 12h;pH 4;	To the solution of 1-formyl-2,4,6-trihydroxy benzene (2) (1.54 g, 10 mmol) intetrahydrofuran (20 mL) we added methyl orange (1±2 drops) followed by the addition of sodiumcyanoborohydride (1.90 g, 30 mmol). The pH of the reaction mixture was maintained at 4.0, throughoutthe reaction, by addition of 1 N HCl. The reaction mixture was stirred at room temperature for 12 hprior to extraction with ethyl acetate (30 mL x 4). The ethyl acetate layer was washed with brinesolution (30 mL x 3) and finally dried over Na2SO4. Solvent was evaporated to get the crude product,which was purified by column chromatography with hexane/EtOAc (50:50 v/v).

68%	With sodium cyanoborohydride; In tetrahydrofuran; at 0 - 20℃;	To a solution of 16 (1.4 g, 9.1 mmol) in THF (25 ml) was added sodium cyanoborohydride (1.7 g, 27.3 mmol) and methyl orange as PH indicator at 0 C in an ice bath, and 1N hydrochloric acid was added to keep the reaction mixture red (acidic environment). Remove ice bath and the solution was stirred until consumption of the starting material. THF was removed under reduced pressure to give the residue, which was extracted with ethyl acetate and dried over anhydrous Na2SO4, And then filtration and concentration in vacuo gave a residue, which was purified by flash column chromatography on silica gel (petroleum ether-EtOAc, 10:1) to yield 19 (865 mg, 68%) as a white solid. 1H NMR (500 MHz, DMSO) delta 8.84 (s, 2H), 8.71 (s, 1H), 5.76 (s, 2H), 1.79 (s, 3H). 13C NMR (126 MHz, DMSO) delta 156.9, 155.9, 101.2, 94.5, 8.5.
68.3%	With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; water; at 20℃; for 1h;	Intermediate 1 (10.04 mmol) was dissolved in 200 mL of THF, and sodium cyanoborohydride (50 mmol) was added with stirring. The reaction mixture turned from orange red to white, then gradually yellowed. At this time, 2N HCl was added dropwise to the reaction solution. Immediately whitened, then gradually yellowed, and then 2N HCl was added dropwise until the reaction solution no longer turned yellow, stirring at room temperature for 1 h, the reaction was stopped, filtered, concentrated under reduced pressure, extracted, concentrated under reduced pressure, silica gel column chromatography Petroleum ether / ethyl acetate = 5:1) obtained white solid 2, yield: 68.3%,
37%	With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; water; at 20℃; for 20h;pH 4;	Toa solution of <strong>[487-70-7]2,4,6-trihydroxy benzaldehyde</strong> (1.54 g, 10 mmol) in THF (30 ml) and sodium cyanoborohydride (1.9 g, 30 mmol). The solution was stirred for 20 h(keeping the pH 4.0) by adding 1N HCl. The reaction mixture was extracted with EtOAc and were washed with brine, dried over Na2SO4 and concentrated under vacuum. The residue was chromatographed on silica gel withpetroleum ether-EtOAc (3:1 to 1:1 v/v) to provide 3 (520 mg, 37%), colorless prisms. Compound was characterized by comparing its data with literature values.

Reference： [1]Patent: CN108947787,2018,A .Location in patent: Paragraph 0017
[2]Patent: CN108997099,2018,A .Location in patent: Paragraph 0009; 0023
[3]Molecules,2018,vol. 23
[4]Tetrahedron Letters,2016,vol. 57,p. 1856 - 1859
[5]Patent: CN109293493,2019,A .Location in patent: Paragraph 0270; 0271; 0274; 0275
[6]Australian Journal of Chemistry,2005,vol. 58,p. 551 - 555
[7]Organic and biomolecular chemistry,2020,vol. 18,p. 1135 - 1139
[8]Tetrahedron Letters,2006,vol. 47,p. 8263 - 8266
[9]Journal of Natural Products,2020,vol. 83,p. 3 - 7
[10]ChemMedChem,2020,vol. 15,p. 1078 - 1088
[11]Angewandte Chemie - International Edition,2018,vol. 57,p. 14650 - 14653
Angew. Chem.,2018,vol. 130,p. 14861 - 14864,4
[12]Phytochemistry,1998,vol. 49,p. 1699 - 1704
[13]Synthetic Communications,2014,vol. 44,p. 3139 - 3147
[14]Chemische Berichte,1942,vol. 75,p. 29,31
[15]Synthetic Communications,1985,vol. 15,p. 1315 - 1324
[16]Phytochemistry,1989,vol. 28,p. 1287 - 1288
[17]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 1750 - 1760
[18]ACS Infectious Diseases,2019,vol. 5,p. 1087 - 1104

3
[ 487-70-7 ]
[ 108-24-7 ]
[ 164329-24-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	dmap; In ethyl acetate;Heating / reflux;	<strong>[487-70-7]2,4,6-Trihydroxybenzaldehyde</strong> (4) (4.62 g, 30 mmoi), acetic anhydride (6.13 g, 60 mmol) and a catalytic amount of N, N-dimethylaminopyridine (DMAP) in dry ethyl acetate (EtOAc) (100 mL) were refiuxed overnight. The reaction mixture was filtrated, water (50 mL) was added and the water phase extracted with EtOAc (4 x 25 mL). The combined organic phases were washed with water (2 x 25 mL) and dried (MgSO4). The crude product was recrystallized from 1 ,2-dimethoxyethane (DME) to give the titled compound as white crystals, m.p. 103-105 0C. Yield 4.3 g. (60%). 1H NMR (300 MHz, CDCl3): delta = 2.29 (3H, s), 2.36 (3H, s), 6.61 (IH5 s), 6.63 (IH, s), 10.04 (IH, s), 11.77 (IH5 s); EPO <DP n="24"/>13C NMR (75 MHz): delta = 20.6 (CH3), 21.0 (CH3), 107.6 (CH), 108.1 (CH), 111.0 (C)3 153.5 (C), 157.2 (C), 163.9 (C), 169.7 (C=O)5 168.1 (C=O), 191.8 (HCO).

Reference： [1]Helvetica Chimica Acta,1994,vol. 77,p. 1595 - 1610
[2]Patent: WO2006/134352,2006,A1 .Location in patent: Page/Page column 18; 22-23
[3]Tetrahedron Letters,2013,vol. 54,p. 2865 - 2869
[4]Journal of Medicinal Chemistry,1999,vol. 42,p. 2662 - 2672
[5]Journal of the Chemical Society,1930,p. 796,811
[6]Bulletin of the Chemical Society of Japan,1941,vol. 16,p. 284,288
[7]Journal of the Chemical Society,1927,p. 1713

4
[ 487-70-7 ]
[ 77-78-1 ]
[ 708-76-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate In N,N-dimethyl-formamide
	With sodium carbonate; acetone

Reference： [1]Dong, Yi; Du, Nana; Li, Xueyuan; Zheng, Litao; Liu, Gang [Organic Letters, 2015, vol. 17, # 16, p. 4110 - 4113]
[2]Karrer; Lichtenstein; Helfenstein [Helvetica Chimica Acta, 1929, vol. 12, p. 991]

5
[ 487-70-7 ]
[ 32136-81-5 ]
[ 13544-50-8 ]

Reference： [1]Helvetica Chimica Acta,1994,vol. 77,p. 1595 - 1610

6
[ 548-83-4 ]
[ 487-70-7 ]
[ 65-85-0 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 9303 - 9314

7
[ 440-60-8 ]
[ 487-70-7 ]
[ 135351-90-5 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 11097 - 11112

8
[ 487-70-7 ]
[ 107-30-2 ]
[ 212265-19-5 ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 2861 - 2869
[2]Journal of Natural Products,2015,vol. 78,p. 1969 - 1976
[3]Journal of the American Chemical Society,1999,vol. 121,p. 7729 - 7746
[4]Angewandte Chemie - International Edition,2015,vol. 54,p. 12678 - 12682
Angew. Chem.,2015,vol. 127,p. 12869 - 12873,5
[5]Organic Letters,2009,vol. 11,p. 587 - 588
[6]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3151 - 3153

9
[ 108-73-6 ]
[ 68-12-2 ]
[ 487-70-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With trichlorophosphate; In ethyl acetate; at 0 - 20℃; for 2h;Inert atmosphere;	To a solution of 15 (1.9 g, 15 mmol) in EtOAc (20 ml) was added DMF (1.26 ml, 16.5 mmol) and POCl3 (1.5 ml, 16.5 mmol) at 0 C in an ice bath. Remove ice bath and the solution was stirred for 2 h. Water was added and the reaction mixture was refluxed for 30 min. When the solution cooled down, ethyl acetate was added to extract. The organic layers were combined and washed with brine, and dried over anhydrous Na2SO4. And then filtration and concentration in vacuo gave a residue, which was purified by flash column chromatography on silica gel (petroleum ether-EtOAc, 4:1) to yield 16 (2.12 g, 92%) as a white solid. 1H NMR (500 MHz, DMSO) delta 9.92 (s, 1H), 5.78 (s, 2H). 13CNMR (126 MHz, DMSO) delta 191.4, 167.6, 164.5, 105.0, 94.6.
83%	With trichlorophosphate; In water; ethyl acetate;	Example 1 - Synthesis of Phloroglucinaldehyde (III) 9 l (1.47 kg, 96.4 moles) of phosphorus oxychloride are added to a solution containing 11.2 kg (88.9 moles) of anhydrous phloroglucinol (II) and 7.5 l (7 kg, 96.4 moles) of N,N-dimethylformamide in 33 l of ethyl acetate. The precipitated solid is filtered and the residue is dissolved in hot water. After cooling to room temperature, the crystallizate is filtered. 11.4 kg of III are obtained (yield: 83%) having a m.p. of 185-186C, E
80%	With trichlorophosphate; at 20℃; for 4h;Inert atmosphere; Cooling with ice;	A 100?mL round bottom flask was charged with phloroglucin (3?g, 24?mmol) and DMF (30?mL). After the flask was flushed with Ar and covered with the rubber plug, POCl3 (2.2?mL, 24?mmol) was added dropwise under the condition of ice bath. After completion of adding, the mixture was stirred at room temperature for 4?h. TLC analysis indicated that the reaction was completed. After quenching the reaction mixture with ice cold water (50?mL), the slurry was extracted with CH2Cl2 (20?mL??3). The combined organic extracts were washed with 20% LiCl aqueous solution (10?mL??2), brine and then dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate?=?2:1) to provide 2,4,6-trihydroxybenzaldehyde (2.9?g, 80%) as a white solid. 1H NMR (300?MHz, DMSO-d6) delta 11.46 (s, 2H), 10.65 (s, 1H), 9.93 (s, 1H), 5.79 (s, 2H). 13C NMR (75?MHz, DMSO-d6) delta 190.9, 167.2, 164.1, 104.6, 94.2. MS (ESI): m/z 153.0 [M-H]-.

80.8%	With trichlorophosphate; In 1,4-dioxane; at 20℃; for 2h;Cooling with ice;	DMF (15 mmol) was placed in a round bottom flask, and POCl3 (15 mmol) was slowly added dropwise in an ice bath, and the mixture was stirred at room temperature for 30 min.The reaction solution of the above DMF and POCl3 was slowly added dropwise to a solution of phloroglucin (15 mmol) in 1,4-dioxane 6 mL under ice bath, and stirred at room temperature for 2 h to stop the reaction, and the reaction solution was poured into 100 mL of ice water, standing still, to precipitate crystals, and then filtered, to obtain 11.867 g of orange-red needle-like crystals, yield: 80.8%,
70%	With trichlorophosphate; In ethyl acetate; at 0 - 20℃; for 7h;Inert atmosphere;	To a cooled (0 C) solution of phloroglucinol (13) (20.0 g, 0.159 mol) and DMF (12.2 mL, 0.159 mol) in EtOAc (300 mL), POCl3 (14.83 mL, 0.159 mol) was added dropwise within 60 min. After complete addition the resulting suspension was left to stir at room temperature for 6 h. When full consumption was achieved, the yellow suspension was poured on ice-water (500 mL), and the two-phase mixture was stirred vigorously while adding satd. NaOAc solution to it until a pH of 5-6 was reached. During the addition the solution became dark-red, then it was extracted with EtOAc (4600 mL). The combined organic layers were washed with satd. NaCl solution (1500 mL), dried over Na2SO4, filtered, and evaporated to dryness. The residue was recrystallized from water (200 mL) to provide benzaldehyde 26 (17.18 g, 70%) as red crystals. 1H NMR (400 MHz, DMSO-d6): delta=5.78 (s, 2H, 3-H), 9.92 (s, 1H, CHO), 10.64 (s, 1H, OH), 11.45 (s, 2H, OH); 13C NMR (100 MHz, DMSO-d6): delta=94.1 (C-3), 104.5 (C-1), 164.1 (C-2), 167.2 (C-4), 190.9 (CHO).
	With trichlorophosphate; In water; ethyl acetate; at 20℃; for 1h;Cooling with ice;	To a 1 L single-necked flask, anhydrous phloroglucinol (30 g, 0.238 mol), DMF (36.68 mL, 0.475 mol), water (4.29 mL, 0.237 mol), ethyl acetate (450 mL) Phosphorus oxychloride (44.21 mL, 0.475 mol) was slowly added dropwise under ice bath. After the addition, the mixture was transferred to room temperature for 1 h, filtered, and washed with ethyl acetate. The filter cake was placed in a 500 mL single-necked flask, and water (150 mL) was added. Nitrogen protection, warmed to reflux for 10 min, naturally cooled to room temperature, placed in a refrigerator for 1 h, filtered, washed with water, and the filter cake was collected and dried in vacuo to give a white solid, 36 g, yield 98%.

Reference： [1]Organic Letters,2015,vol. 17,p. 4110 - 4113
[2]Tetrahedron Letters,2016,vol. 57,p. 1856 - 1859
[3]Organic and biomolecular chemistry,2020,vol. 18,p. 1135 - 1139
[4]Synthetic Communications,1998,vol. 28,p. 2861 - 2869
[5]Organic Letters,2010,vol. 12,p. 1676 - 1679
[6]Synlett,2007,p. 129 - 130
[7]Patent: EP348121,1989,A1
[8]Molecules,2018,vol. 23
[9]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 116 - 124
[10]Patent: CN109293493,2019,A .Location in patent: Paragraph 0270-0273
[11]Australian Journal of Chemistry,2005,vol. 58,p. 551 - 555
[12]Tetrahedron,2015,vol. 71,p. 9662 - 9666
[13]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3151 - 3153
[14]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 1750 - 1760
[15]Patent: CN108997099,2018,A .Location in patent: Paragraph 0009; 0022
[16]ACS Infectious Diseases,2019,vol. 5,p. 1087 - 1104

10
[ 487-70-7 ]
[ 85117-87-9 ]
[ 528-53-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol

Reference： [1]Reichel; Burkhart [Justus Liebigs Annalen der Chemie, 1938, vol. 536, p. 164,168]

11
[ 111-83-1 ]
[ 487-70-7 ]
2,4,6-tris(octyloxy)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 70℃; for 24h;	<strong>[487-70-7]2,4,6-Trihydroxybenzaldehyde</strong> (305 mg, 1.77 mmol), 1-bromooctane (2.03 g, 10.5 mmol), K2CO3 (732 mg, 530 mmol) and KI (50 mg, 0.30 mmol) were mixed in DMF (15 ml), followed by stirring at 70 C. for 24 hours. The subsequent operations are the same as in Example 1 and are therefore omitted to describe. Thus, yellow oily 2,4,6-trioctyloxybenzaldehyde (1a') was obtained (700 mg, yield: 81%). It was confirmed by 1H NMR quantitative analysis that 1a' is 2,4,6-trioctyloxybenzaldehyde.

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10384 - 10385
[2]Patent: US2010/19205,2010,A1 .Location in patent: Page/Page column 6
[3]Langmuir,2013,vol. 29,p. 5337 - 5344

12
[ 487-70-7 ]
[ 143-15-7 ]
2,4,6-tris(dodecyloxy)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 70℃; for 20h;	<strong>[487-70-7]2,4,6-Trihydroxybenzaldehyde</strong> (250 mg, 1.45 mmol), 1-bromododecane (2.15 g, 8.63 mmol), K2CO3 (600 mg, 4.34 mmol) and KI (40 mg, 0.24 mmol) were mixed in DMF (10 ml), followed by stirring at 70 C. for 20 hours. The resulting reaction product was cooled to 20 C., and chloroform (50 ml) was added thereto to separate into an organic phase and an aqueous phase. Only the organic phase was washed with salt water (100 ml) two times, and then dried using Na2SO4. The resulting crude product was purified by column chromatography (silica gel, hexane/CH2Cl2=1:1) to obtain yellow oily 2,4,6-tridecyloxybenzaldehyde (1a) (460 mg, yield: 48%). It was confirmed by 1H NMR quantitative analysis that 1a is 2,4,6-tridodecyloxybenzaldehyde.

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10384 - 10385
[2]Patent: US2010/19205,2010,A1 .Location in patent: Page/Page column 4-6
[3]Angewandte Chemie - International Edition,2012,vol. 51,p. 3391 - 3395
[4]Langmuir,2013,vol. 29,p. 5337 - 5344

13
[ 487-70-7 ]
[ 112-82-3 ]
2,4,6-tris(hexadecyloxy)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 70℃; for 20h;	<strong>[487-70-7]2,4,6-Trihydroxybenzaldehyde</strong> (435 mg, 2.53 mmol), 1-bromohexadecane (4.58 g, 15.0 mmol), K2CO3 (1.04 g, 4.52 mmol) and KI (70 mg, 0.42 mmol) were mixed in DMF (15 ml), followed by stirring at 70 C. for 20 hours. The resulting reaction product was cooled to 20 C., and chloroform (100 ml) was added thereto to separate into an organic phase and an aqueous phase. The subsequent operations are the same as in Example 1, and therefore are omitted to describe. Thus, white solid 2,4,6-trihexadecyloxybenzaldehyde (2a) was obtained (1.04 g, yield: 50%). It was confirmed by 1H NMR quantitative analysis that 2a is 2,4,6-trihexadecyloxybenzaldehyde.

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10384 - 10385
[2]Patent: US2010/19205,2010,A1 .Location in patent: Page/Page column 5; 6
[3]Langmuir,2013,vol. 29,p. 5337 - 5344

14
[ 487-70-7 ]
[ 74-88-4 ]
[ 708-76-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium carbonate; In acetone; at 50℃;	A suspension of <strong>[487-70-7]2,4,6-trihydroxybenzaldehyde</strong> (3.32 g, 21.5 mmol), methyl iodide (6.72 mL, 47.4 mmol) and K2CO3 (5.94 g, 43.3 mmol) in acetone (25 mL) was stirred at 50C until the starting material was completely consumed (TLC). Water was added and the aqueous layer was extracted three times with MTBE (50 mL for each extraction). The combined organic layers were dried with MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica to give 2-hydroxy-4,6-dimethoxybenzaldehyde (2.18 g, 12.0 mmol, 56%). Colourless solid, mp 68 - 70C; 1H NMR (300 MHz, CDCl3) delta 12.48 (s, 1H), 10.06 (s, 1H), 5.98 (d, J = 1.7 Hz, 1H), 5.88 (d, J = 1.8 Hz, 1H), 3.82 (s, 3H), 3.81 (s, 3H); 13C NMR (75 MHz, CDCl3) delta 191.9, 168.3, 166.4, 163.7, 106.1, 93.0, 90.6, 55.8, 55.8

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3281 - 3286
[2]Synthesis,2016,vol. 48,p. 141 - 149

15
[ 487-70-7 ]
[ 528-53-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 21 percent / triethylamine / acetone / 1 h / 0 - 20 °C 2: hydrogen chloride; ethanol / ethyl acetate / 25 h 3: 220 mg / sodium hydroxide / H₂O / 2.25 h / 0 - 20 °C

Reference： [1]Kraus, Michael; Biskup, Ellen; Richling, Elke; Schreier, Peter [Journal of labelled compounds and radiopharmaceuticals, 2006, vol. 49, # 13, p. 1151 - 1162]

16
[ 487-70-7 ]
[ 4049-38-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 75 percent / Et(i-Pr)2N; 4-(dimethylamino)pyridine / CH₂Cl₂ 2.1: magnesium bromide dietherate / diethyl ether 2.2: 45 percent / lithium aluminum hydride / diethyl ether / 3 h / -78 - 20 °C 3.1: 88 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C 4.1: 82 percent / zinc bromide / CH₂Cl₂ / 6 h / 20 °C 5.1: 80 percent / 2-iodoxybenzoic acid; Na₂S₂O₄ / dimethylsulfoxide / 9 h / 20 °C

Reference： [1]Selenski, Carolyn; Pettus, Thomas R.R. [Tetrahedron, 2006, vol. 62, # 22, p. 5298 - 5307]

17
[ 487-70-7 ]
[ 55743-13-0 ]

Reference： [1]Chemische Berichte,1942,vol. 75,p. 29,31
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 14650 - 14653
Angew. Chem.,2018,vol. 130,p. 14861 - 14864,4
[3]Molecules,2018,vol. 23

18
[ 487-70-7 ]
[ 2732-18-5 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1907,vol. 357,p. 373
[2]Tetrahedron Letters,2009,vol. 50,p. 4769 - 4772

19
[ 16649-50-6 ]
[ 487-70-7 ]
[ 198695-59-9 ]

Yield	Reaction Conditions	Operation in experiment
65.5%	With toluene-4-sulfonic acid; In ethyl acetate; benzene;	Example 2 Synthesis of alpha-(2,4,6-Trihydroxyphenyl)-N-tert-butylnitrone 2,4,6-Trihydroxybenzaldehyde (17.69 g, 0.115 mole) was added to a solution of N-tert-butyl hydroxylamine (14.32 g, 0.161 mole) in benzene (250 mL). p-Toluenesulfonic acid (15 mg) was added and the reaction vessel fitted with a Dean-Stark trap. The reaction was heated at reflux for 88 hours under nitrogen and then diluted with 500 mL of ethyl acetate. The solution was washed with water, brine and dried over sodium sulfate. The product was recrystallized from ethanol/water and then dried in vacuo for 2 hr at 35 C. to provide 16.95 g (65.5% yield) of the title compound. The product had a melting point of 189.9-190.3 C. and an Rf on silica gel TLC (50% hexane, 45% ethyl acetate, 5% methanol) of 0.31 (2,4,6-trihydroxybenzaldehyde Rf=0.47).

Reference： [1]Patent: US5972977,1999,A

20
[ 109-87-5 ]
[ 487-70-7 ]
[ 1132988-93-2 ]

Yield	Reaction Conditions	Operation in experiment
65%		Preparation of Ethyl3-[2,4-dihydroxy-6-(4-nitrophenoxy)phenyl]isoxazole-5-carboxylate[(XXXI), (Z)-R=4-Nitrophenoxy, X=N, Y=O, W=CH R^=CO2C2H5]; Step 1; 2-Hydroxy-4,6-bis(methoxymethoxy)benzaldehyde; To a stirred solution of dimethoxymethane (26.4 mL, 30 mmol) and zinc bromide (0.180 g, 0.08 mmol) in dichloromethane (200 mL) was slowly added drop wise acetyl chloride (21.2 mL, 24 mmol) at 100C and the stirring was continued for 1 h at this temperature, then 3 hours at room temperature. The solution was cooled at 5 0C and <strong>[487-70-7]2,4,6-trihydroxybenzaldehyde</strong> (21.1 g, 30 mmol) was added portion wise followed by slow drop wise addition of a solution of DIPEA (83.2 mL, 4.8 eq.). The cloudy solution was stirred overnight, then DCM (200 mL) was added and after washing with NH4CI saturated solution (300 mL) was dried over Na2SO4. Removal of the solvent and filtration over a small pad of silica gel eluting with cyclohexane/ethyl acetate 9/1 afforded the title compound (21 g, 65% yield). 1H NMR (400 MHz, DMSOd6) delta ppm 3.13 (br. s., 2 H) 3.39 (s, 3 H) 3.43 (s, 3 H) 5.24 - 5.28 (m, 2 H) 5.31 (s, 2 H)6.20 (d, 1 H) 6.29 (d, 1 H) 10.07 - 10.17 (m, 1 H) 12.17 (s, 1 H).

Reference： [1]Patent: WO2010/121963,2010,A1 .Location in patent: Page/Page column 66-67

21
[ 487-70-7 ]
[ 1314996-49-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; at 70℃;	General procedure: Hydroxylamine hydrochloride (4 mmol) and Na2CO3 (2 mmol) were mixed together in water (3 mL) until the solid dissolves and the gas emission stops. This aqueous solution was added to the corresponding aldehyde or nitrile (1 mmol) in absolute ethanol (0.5 mL).The mixture was heated at 70 C for 2-24 h. The reaction mixture was then allowed to cool down to room temperature. If the compound precipitated, the solid was filtered off, washed with cold water and dried under vacuum. Otherwise the reaction mixture was extracted with ethyl acetate and dried over Na2SO4. After removal of the solvent the compound was purified by column chromatography (cyclohexane/ethyl acetate) to afford the desired oxime or amidoxime.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6352 - 6361

22
[ 112-29-8 ]
[ 487-70-7 ]
[ 1000607-97-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 110℃; for 48h;	A mixture of <strong>[487-70-7]2,4,6-trihydroxybenzaldehyde</strong> (3.00 g, 19.5 mmol), 1-bromodecane (25.87 g, 117.0 mmol), K2CO3 (8.07 g, 58.4 mmol), and KI (549 mg, 3.3 mmol) in DMF (150 mL) was stirred for 24 h at 110 C. and then one more portion of 1-bromodecane (5.0 g, 22.6 mmol) was added and continued stirring for another 24 h. The reaction mixture was cooled to 20 C. and extracted with CH2Cl2. The organic phase was washed with brine, dried (Na2SO4), and evaporated. Column chromatography (silica gel, hexane/CH2Cl2, 1:1, v/v) afforded the product (9.86 g, 88%) as yellow oil. 1H NMR (400 MHz, CDCl3) delta 10.38 (s, 1H), 6.02 (s, 2H), 3.98 (m, 6H), 1.98-1.66 (m, 6H), 1.44 (m, 6H), 1.40-1.12 (m, 36H), 0.87 (m, 9H). 13C NMR (101 MHz, CDCl3) delta 187.9, 165.8, 163.7, 109.2, 91.5, 69.1, 68.4, 32.1, 29.8, 29.6, 29.6, 29.3, 29.2, 26.2, 22.9, 14.4; HR-MS (ESI): calcd. for C37H66O4 [M+H+]: 575.5034. Found: 575.5033.

Reference： [1]Advanced synthesis and catalysis,2012,vol. 354,p. 2073 - 2078,6
[2]Patent: US2013/261295,2013,A1 .Location in patent: Paragraph 0215; 0216

23
[ 487-70-7 ]
[ 168646-54-6 ]
[ 1426233-06-8 ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 8907 - 8917

24
[ 487-70-7 ]
[ 2632-13-5 ]
[ 491-80-5 ]

Yield	Reaction Conditions	Operation in experiment
65%		General procedure: To prepare catalyst, 0.21 g of thiamine hydrochloride (0.6 mmol) was dissolved in 0.64 mL of water and added 2.4 mLof 95% ethanol (water : 95% ethanol = ~1:4). The solution was cooled in an ice bath, then added 0.40 mL of 3 M NaOH(1.2 mmol) dropwise with stirring in a manner such that thetemperature remained below 20 C. Intense yellow coloured solution changed to pale yellow solution of thiamine (thiazolium ion)/N-heterocyclic carbene (Scheme 1).47 In a 25-mL round bottom flask, a mixture of phenacylbromide 1 (2.5 mmol, 0.5 g in case of 1a) and thiamine (0.6 mmol, 25 mol %) in ethanol (4 mL) was stirred at room temperature for 15 min. Then, salicylaldehyde 2 (2.5 mmol, 0.26 mL in case of 2a) was added slowly and the mixture was stirred at room temperature until the reaction was completed (as monitored by TLC) (Table 3) . The reaction mixture was then poured into 20 mL of distilled water and extracted with ethyl acetate (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The resulting product isoflavone 3 was further purified either by recrystallizationor by column chromatography (Ethyl acetate:Hexane, 1:4v/v). All compounds were characterized by their mp and 1HNMR, 13CNMR and mass spectral data.

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 1070 - 1076

25
[ 2491-38-5 ]
[ 487-70-7 ]
[ 446-72-0 ]

Yield	Reaction Conditions	Operation in experiment
75%		General procedure: To prepare catalyst, 0.21 g of thiamine hydrochloride (0.6 mmol) was dissolved in 0.64 mL of water and added 2.4 mLof 95% ethanol (water : 95% ethanol = ~1:4). The solution was cooled in an ice bath, then added 0.40 mL of 3 M NaOH(1.2 mmol) dropwise with stirring in a manner such that thetemperature remained below 20 C. Intense yellow coloured solution changed to pale yellow solution of thiamine (thiazolium ion)/N-heterocyclic carbene (Scheme 1).47 In a 25-mL round bottom flask, a mixture of phenacylbromide 1 (2.5 mmol, 0.5 g in case of 1a) and thiamine (0.6 mmol, 25 mol %) in ethanol (4 mL) was stirred at room temperature for 15 min. Then, salicylaldehyde 2 (2.5 mmol, 0.26 mL in case of 2a) was added slowly and the mixture was stirred at room temperature until the reaction was completed (as monitored by TLC) (Table 3) . The reaction mixture was then poured into 20 mL of distilled water and extracted with ethyl acetate (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The resulting product isoflavone 3 was further purified either by recrystallizationor by column chromatography (Ethyl acetate:Hexane, 1:4v/v). All compounds were characterized by their mp and 1HNMR, 13CNMR and mass spectral data.

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 1070 - 1076

26
[ 487-70-7 ]
[ 4687-37-0 ]
[ 1456071-26-3 ]

Reference： [1]MedChemComm,2013,vol. 4,p. 993 - 1000

27
[ 487-70-7 ]
[ 4687-37-0 ]
[ 1456071-22-9 ]

Reference： [1]MedChemComm,2013,vol. 4,p. 993 - 1000

28
[ 54-85-3 ]
[ 487-70-7 ]
[ 1263032-77-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With acetic acid; In ethanol;Reflux;	General procedure: Nicotinic/isonicotinic hydrazides (1 mmol), substituted aromatic aldehyde (1 mmol) and glacial acetic acid (few drops) were taken in ethanol (10 mL) and refluxed for 3 h. Progress of the reaction was monitored by TLC. After the completion of the reaction,mixture was left for evaporation of solvent, and then crude product washed with dichloromethane and hexane, and dried to afford compounds 1-54.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 2351 - 2371
[2]Medicinal Chemistry Research,2014,vol. 23,p. 269 - 279

29
[ 27700-58-9 ]
[ 487-70-7 ]
[ 1610624-77-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With trifluoroacetic acid; In ethanol; at 20℃;	General procedure: Compounds 2-4 were synthesized according previously reported procedures, compound 2 is described in Ref. 26, compounds 3 and 4 are described in Ref. 27. TFA (1 equiv) was added to a mixture of compound 4 (0.40 g, 1 equiv) and aldehyde 5 (1.1 equiv) in ethanol (5 mL), at room temperature under stirring. When TLC showed the absence of the reagent, the solid was filtered and washed with ethanol and was identified as 5. Compound 6a: Yield 70%; mp: 236-238C; IR (Nujol mull) (numax/cm-1): 3299, 2229, 1586, 1519. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 10.01 (s, 1H, OH), 9.49 (s, 1H, OH), 8.71 (s, 1H, N=CH), 7.78 (s, 1H, H-2), 7.44 (d, J=1.8Hz, 1H, ArH), 7.26 (dd, J=8.3/1.8Hz, 1H, ArH), 6.88 (d, J=8.4Hz, 1H, ArH), 3.59 (s, 3H, Me). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 164(Cimin), 151, 148(C-5), 146, 138(C-2), 127, 124, 117, 116(CN), 114, 97(C-4), 31. Anal. Calcd for C12H10N4O2: C, 59.50; H, 4.13; N, 23.14. Found: C, 59.55; H, 4.34; N, 22.98. Compound 6b: Yield 80%; mp: 242-244C; IR (Nujol mull) (numax/cm-1): 3555, 3270, 2215, 1586, 1533, 1515. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 9.39 (br s, 2H, OH), 9.19 (br s, 1H, OH), 8.63 (s, 1H, N=CH), 7.78 (s, 1H, H-2), 6.95 (s, 2H, ArH), 3.59 (s, 3H, Me). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 148(C-5), 146, 139, 138(C-2), 125, 117(CN), 109, 97(C-4), 31. Anal. Calcd for C12H10N4O3.0.9H2O: C, 52.65; H, 4.43; N, 20.72. Found: C, 52.52; H, 4.30; N, 20.42. Compound 6c: Yield 70%; mp: >275 (dec.) C; IR (Nujol mull) (numax/cm-1): 3453, 3120, 2227, 1636, 1601, 1525. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.25 (s, 1H, OH), 10.18 (s, 1H, OH), 8.71 (br s, 1H, OH), 8.98 (s, 1H, N=CH), 7.79 (s, 1H, H-2), 7.14 (d, J=8.7Hz, 1H, ArH), 6.48 (d, J=8.7Hz, 1H, ArH), 3.60 (s, 3H, Me). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 164(Cimin), 152, 150, 147(C-5), 138(C-2), 133, 123, 116(CN), 113, 109, 98(C-4), 31. Anal. Calcd for C12H10N4O3: C, 55.81; H, 3.87; N, 21.70. Found: C, 55.74; H, 4.05; N, 21.58. Compound 6d: Yield 68%; mp: >260 (dec.) C; IR (Nujol mull) (numax/cm-1): 3364, 3108, 2227, 1648, 1609, 1577, 1564. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.62 (s, 2H, OH), 10.51 (s, 1H, OH), 9.24 (s, 1H, N=CH), 7.76 (s, 1H, H-2), 5.87 (s, 2H, ArH), 3.56 (s, 3H, Me). 13C NMR (DMSO-d6, 100 MHz): deltaC (ppm) 166(Cimin), 163, 161, 147(C-5), 138(C-2), 117(CN), 102, 98(C-4), 95, 31. Anal. Calcd for C12H10N4O3.0.1H2O: C, 55.43; H, 3.93; N, 21.56. Found: C, 55.47; H, 4.26; N, 21.18. Compound 6e: Yield 55%; mp: 285-287C; IR (Nujol mull) (numax/cm-1): 3433, 3127, 2231, 1611, 1591, 1521. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 9.97 (s, 1H, OH), 9.90 (s, 1H, OH), 9.47 (s, 1H, OH), 8.72 (s, 1H, N=CH), 8.01 (s, 1H, H-2), 7.30 (d, J=7.0Hz, 2H, ArH), 7.27 (d, J=2.1Hz, 1H, ArH), 7.17 (dd, J=8.4/2.1Hz, 1H, ArH), 6.88 (d, J=7.0Hz, 2H, ArH), 6.85 (d, J=8.4Hz, 1H, ArH). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 158, 151, 148(C-5), 146, 137(C-2), 127, 126.6, 126, 124, 117(CN), 116, 114, 115.7, 98(C-4). Anal. Calcd for C17H12N4O3.0.4H2O: C, 62.52; H, 3.89; N, 17.16. Found: C, 62.39; H, 3.96; N, 16.92. Compound 6f: Yield 81%; mp: 285-287C; IR (Nujol mull) (numax/cm-1): 3309, 2238, 1605, 1586, 1519. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) delta 9.91 (s, 1H, OH), 9.37 (br s, 2H, OH), 9.16 (br s, 1H, OH), 8.64 (s, 1H, N=CH), 7.99 (s, 1H, H-2), 7.29 (d, J=9.0Hz, 2H, ArH), 6.88 (d, J=9.0Hz, 2H, ArH), 6.82 (s, 2H, ArH). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 158, 149(C-5), 146, 139, 137(C-2), 127, 126, 125, 117(CN), 116, 109, 98(C-4). Anal. Calcd for C17H12N4O4: C, 60.71; H, 3.57; N, 16.67. Found: C, 60.55; H, 3.71; N, 16.69. Compound 6g: Yield 98%; mp: 289-291C; IR (Nujol mull) (numax/cm-1): 3355, 3126, 2218, 1633, 1606, 1524, 1501. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.24 (s, 1H, OH), 10,15 (s, 1H, OH), 8.99 (s, 1H, N=CH),9.97 (s, 1H, OH), 8.68 (s, 1H, OH), 8.01 (s, 1H, H-2), 7.32 (d, J=8.7Hz, 2H, ArH), 7.01 (d, J=9.0Hz, 1H, ArH), 6.89 (d, J=8.7Hz, 2H, ArH), 6.45 (d, J=9.0Hz, 1H, ArH). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 158, 152, 150, 147(C-5), 138(C-2), 132, 127, 125, 124, 117(CN), 116, 112, 109, 99(C-4). Anal. Calcd for C17H12N4O4.1.8H2O: C, 55.37; H, 4.23; N, 15.20. Found: C, 55.10; H, 4.34; N, 15.08. Compound 6h: Yield 86%; mp: 300C (dec.); IR (Nujol mull) (numax/cm-1): 3368, 3302, 3141, 2227, 1652, 1609, 1582, 1568, 1522. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.43 (s, 2H, OH), 10.48 (s, 1H, OH), 9.96 (s, 1H, OH), 9.31 (s, 1H, N=CH), 7.96 (s, 1H, H-2), 7.29 (d, J=9.0Hz, 2H, ArH), 6.88 (d, J=9.0Hz, 2H, ArH), 5.79 (s, 2H, ArH). 13C NMR(DMSO-d6, 100MHz): deltaC (ppm) 166(Cimin), 163, 161, 158, 147(C-5), 137(C-2), 127, 125, 117(CN), 116, 102, 98(C-4), 95. Anal. Calcd for C17H12N4O4.0.6H2O: C, 58.82; H, 3.81; N, 16.15. Found: C, 58.74; H, 3.91; N, 16.15. Compound 6i: Yield 42%; mp: 253-255C; IR (Nujol mull) (numax/cm-1): 3475, 3133, 2223, 1608, 1584. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 9.70 (br s, 2H, OH), 8.73 (s, 1H, N=CH), 8.05 (s, 1H, H-2),...

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2768 - 2772

30
[ 487-70-7 ]
[ 849110-27-6 ]
[ 1610624-81-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With trifluoroacetic acid; In ethanol; at 20℃;	General procedure: Compounds 2-4 were synthesized according previously reported procedures, compound 2 is described in Ref. 26, compounds 3 and 4 are described in Ref. 27. TFA (1 equiv) was added to a mixture of compound 4 (0.40 g, 1 equiv) and aldehyde 5 (1.1 equiv) in ethanol (5 mL), at room temperature under stirring. When TLC showed the absence of the reagent, the solid was filtered and washed with ethanol and was identified as 5. Compound 6a: Yield 70%; mp: 236-238C; IR (Nujol mull) (numax/cm-1): 3299, 2229, 1586, 1519. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 10.01 (s, 1H, OH), 9.49 (s, 1H, OH), 8.71 (s, 1H, N=CH), 7.78 (s, 1H, H-2), 7.44 (d, J=1.8Hz, 1H, ArH), 7.26 (dd, J=8.3/1.8Hz, 1H, ArH), 6.88 (d, J=8.4Hz, 1H, ArH), 3.59 (s, 3H, Me). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 164(Cimin), 151, 148(C-5), 146, 138(C-2), 127, 124, 117, 116(CN), 114, 97(C-4), 31. Anal. Calcd for C12H10N4O2: C, 59.50; H, 4.13; N, 23.14. Found: C, 59.55; H, 4.34; N, 22.98. Compound 6b: Yield 80%; mp: 242-244C; IR (Nujol mull) (numax/cm-1): 3555, 3270, 2215, 1586, 1533, 1515. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 9.39 (br s, 2H, OH), 9.19 (br s, 1H, OH), 8.63 (s, 1H, N=CH), 7.78 (s, 1H, H-2), 6.95 (s, 2H, ArH), 3.59 (s, 3H, Me). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 148(C-5), 146, 139, 138(C-2), 125, 117(CN), 109, 97(C-4), 31. Anal. Calcd for C12H10N4O3.0.9H2O: C, 52.65; H, 4.43; N, 20.72. Found: C, 52.52; H, 4.30; N, 20.42. Compound 6c: Yield 70%; mp: >275 (dec.) C; IR (Nujol mull) (numax/cm-1): 3453, 3120, 2227, 1636, 1601, 1525. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.25 (s, 1H, OH), 10.18 (s, 1H, OH), 8.71 (br s, 1H, OH), 8.98 (s, 1H, N=CH), 7.79 (s, 1H, H-2), 7.14 (d, J=8.7Hz, 1H, ArH), 6.48 (d, J=8.7Hz, 1H, ArH), 3.60 (s, 3H, Me). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 164(Cimin), 152, 150, 147(C-5), 138(C-2), 133, 123, 116(CN), 113, 109, 98(C-4), 31. Anal. Calcd for C12H10N4O3: C, 55.81; H, 3.87; N, 21.70. Found: C, 55.74; H, 4.05; N, 21.58. Compound 6d: Yield 68%; mp: >260 (dec.) C; IR (Nujol mull) (numax/cm-1): 3364, 3108, 2227, 1648, 1609, 1577, 1564. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.62 (s, 2H, OH), 10.51 (s, 1H, OH), 9.24 (s, 1H, N=CH), 7.76 (s, 1H, H-2), 5.87 (s, 2H, ArH), 3.56 (s, 3H, Me). 13C NMR (DMSO-d6, 100 MHz): deltaC (ppm) 166(Cimin), 163, 161, 147(C-5), 138(C-2), 117(CN), 102, 98(C-4), 95, 31. Anal. Calcd for C12H10N4O3.0.1H2O: C, 55.43; H, 3.93; N, 21.56. Found: C, 55.47; H, 4.26; N, 21.18. Compound 6e: Yield 55%; mp: 285-287C; IR (Nujol mull) (numax/cm-1): 3433, 3127, 2231, 1611, 1591, 1521. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 9.97 (s, 1H, OH), 9.90 (s, 1H, OH), 9.47 (s, 1H, OH), 8.72 (s, 1H, N=CH), 8.01 (s, 1H, H-2), 7.30 (d, J=7.0Hz, 2H, ArH), 7.27 (d, J=2.1Hz, 1H, ArH), 7.17 (dd, J=8.4/2.1Hz, 1H, ArH), 6.88 (d, J=7.0Hz, 2H, ArH), 6.85 (d, J=8.4Hz, 1H, ArH). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 158, 151, 148(C-5), 146, 137(C-2), 127, 126.6, 126, 124, 117(CN), 116, 114, 115.7, 98(C-4). Anal. Calcd for C17H12N4O3.0.4H2O: C, 62.52; H, 3.89; N, 17.16. Found: C, 62.39; H, 3.96; N, 16.92. Compound 6f: Yield 81%; mp: 285-287C; IR (Nujol mull) (numax/cm-1): 3309, 2238, 1605, 1586, 1519. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) delta 9.91 (s, 1H, OH), 9.37 (br s, 2H, OH), 9.16 (br s, 1H, OH), 8.64 (s, 1H, N=CH), 7.99 (s, 1H, H-2), 7.29 (d, J=9.0Hz, 2H, ArH), 6.88 (d, J=9.0Hz, 2H, ArH), 6.82 (s, 2H, ArH). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 158, 149(C-5), 146, 139, 137(C-2), 127, 126, 125, 117(CN), 116, 109, 98(C-4). Anal. Calcd for C17H12N4O4: C, 60.71; H, 3.57; N, 16.67. Found: C, 60.55; H, 3.71; N, 16.69. Compound 6g: Yield 98%; mp: 289-291C; IR (Nujol mull) (numax/cm-1): 3355, 3126, 2218, 1633, 1606, 1524, 1501. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.24 (s, 1H, OH), 10,15 (s, 1H, OH), 8.99 (s, 1H, N=CH),9.97 (s, 1H, OH), 8.68 (s, 1H, OH), 8.01 (s, 1H, H-2), 7.32 (d, J=8.7Hz, 2H, ArH), 7.01 (d, J=9.0Hz, 1H, ArH), 6.89 (d, J=8.7Hz, 2H, ArH), 6.45 (d, J=9.0Hz, 1H, ArH). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 158, 152, 150, 147(C-5), 138(C-2), 132, 127, 125, 124, 117(CN), 116, 112, 109, 99(C-4). Anal. Calcd for C17H12N4O4.1.8H2O: C, 55.37; H, 4.23; N, 15.20. Found: C, 55.10; H, 4.34; N, 15.08. Compound 6h: Yield 86%; mp: 300C (dec.); IR (Nujol mull) (numax/cm-1): 3368, 3302, 3141, 2227, 1652, 1609, 1582, 1568, 1522. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.43 (s, 2H, OH), 10.48 (s, 1H, OH), 9.96 (s, 1H, OH), 9.31 (s, 1H, N=CH), 7.96 (s, 1H, H-2), 7.29 (d, J=9.0Hz, 2H, ArH), 6.88 (d, J=9.0Hz, 2H, ArH), 5.79 (s, 2H, ArH). 13C NMR(DMSO-d6, 100MHz): deltaC (ppm) 166(Cimin), 163, 161, 158, 147(C-5), 137(C-2), 127, 125, 117(CN), 116, 102, 98(C-4), 95. Anal. Calcd for C17H12N4O4.0.6H2O: C, 58.82; H, 3.81; N, 16.15. Found: C, 58.74; H, 3.91; N, 16.15. Compound 6i: Yield 42%; mp: 253-255C; IR (Nujol mull) (numax/cm-1): 3475, 3133, 2223, 1608, 1584. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 9.70 (br s, 2H, OH), 8.73 (s, 1H, N=CH), 8.05 (s, 1H, H-2),...

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2768 - 2772

31
[ 487-70-7 ]
[ 155579-43-4 ]
[ 1610624-88-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With trifluoroacetic acid; In ethanol; at 20℃;	General procedure: Compounds 2-4 were synthesized according previously reported procedures, compound 2 is described in Ref. 26, compounds 3 and 4 are described in Ref. 27. TFA (1 equiv) was added to a mixture of compound 4 (0.40 g, 1 equiv) and aldehyde 5 (1.1 equiv) in ethanol (5 mL), at room temperature under stirring. When TLC showed the absence of the reagent, the solid was filtered and washed with ethanol and was identified as 5. Compound 6a: Yield 70%; mp: 236-238C; IR (Nujol mull) (numax/cm-1): 3299, 2229, 1586, 1519. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 10.01 (s, 1H, OH), 9.49 (s, 1H, OH), 8.71 (s, 1H, N=CH), 7.78 (s, 1H, H-2), 7.44 (d, J=1.8Hz, 1H, ArH), 7.26 (dd, J=8.3/1.8Hz, 1H, ArH), 6.88 (d, J=8.4Hz, 1H, ArH), 3.59 (s, 3H, Me). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 164(Cimin), 151, 148(C-5), 146, 138(C-2), 127, 124, 117, 116(CN), 114, 97(C-4), 31. Anal. Calcd for C12H10N4O2: C, 59.50; H, 4.13; N, 23.14. Found: C, 59.55; H, 4.34; N, 22.98. Compound 6b: Yield 80%; mp: 242-244C; IR (Nujol mull) (numax/cm-1): 3555, 3270, 2215, 1586, 1533, 1515. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 9.39 (br s, 2H, OH), 9.19 (br s, 1H, OH), 8.63 (s, 1H, N=CH), 7.78 (s, 1H, H-2), 6.95 (s, 2H, ArH), 3.59 (s, 3H, Me). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 148(C-5), 146, 139, 138(C-2), 125, 117(CN), 109, 97(C-4), 31. Anal. Calcd for C12H10N4O3.0.9H2O: C, 52.65; H, 4.43; N, 20.72. Found: C, 52.52; H, 4.30; N, 20.42. Compound 6c: Yield 70%; mp: >275 (dec.) C; IR (Nujol mull) (numax/cm-1): 3453, 3120, 2227, 1636, 1601, 1525. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.25 (s, 1H, OH), 10.18 (s, 1H, OH), 8.71 (br s, 1H, OH), 8.98 (s, 1H, N=CH), 7.79 (s, 1H, H-2), 7.14 (d, J=8.7Hz, 1H, ArH), 6.48 (d, J=8.7Hz, 1H, ArH), 3.60 (s, 3H, Me). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 164(Cimin), 152, 150, 147(C-5), 138(C-2), 133, 123, 116(CN), 113, 109, 98(C-4), 31. Anal. Calcd for C12H10N4O3: C, 55.81; H, 3.87; N, 21.70. Found: C, 55.74; H, 4.05; N, 21.58. Compound 6d: Yield 68%; mp: >260 (dec.) C; IR (Nujol mull) (numax/cm-1): 3364, 3108, 2227, 1648, 1609, 1577, 1564. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.62 (s, 2H, OH), 10.51 (s, 1H, OH), 9.24 (s, 1H, N=CH), 7.76 (s, 1H, H-2), 5.87 (s, 2H, ArH), 3.56 (s, 3H, Me). 13C NMR (DMSO-d6, 100 MHz): deltaC (ppm) 166(Cimin), 163, 161, 147(C-5), 138(C-2), 117(CN), 102, 98(C-4), 95, 31. Anal. Calcd for C12H10N4O3.0.1H2O: C, 55.43; H, 3.93; N, 21.56. Found: C, 55.47; H, 4.26; N, 21.18. Compound 6e: Yield 55%; mp: 285-287C; IR (Nujol mull) (numax/cm-1): 3433, 3127, 2231, 1611, 1591, 1521. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 9.97 (s, 1H, OH), 9.90 (s, 1H, OH), 9.47 (s, 1H, OH), 8.72 (s, 1H, N=CH), 8.01 (s, 1H, H-2), 7.30 (d, J=7.0Hz, 2H, ArH), 7.27 (d, J=2.1Hz, 1H, ArH), 7.17 (dd, J=8.4/2.1Hz, 1H, ArH), 6.88 (d, J=7.0Hz, 2H, ArH), 6.85 (d, J=8.4Hz, 1H, ArH). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 158, 151, 148(C-5), 146, 137(C-2), 127, 126.6, 126, 124, 117(CN), 116, 114, 115.7, 98(C-4). Anal. Calcd for C17H12N4O3.0.4H2O: C, 62.52; H, 3.89; N, 17.16. Found: C, 62.39; H, 3.96; N, 16.92. Compound 6f: Yield 81%; mp: 285-287C; IR (Nujol mull) (numax/cm-1): 3309, 2238, 1605, 1586, 1519. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) delta 9.91 (s, 1H, OH), 9.37 (br s, 2H, OH), 9.16 (br s, 1H, OH), 8.64 (s, 1H, N=CH), 7.99 (s, 1H, H-2), 7.29 (d, J=9.0Hz, 2H, ArH), 6.88 (d, J=9.0Hz, 2H, ArH), 6.82 (s, 2H, ArH). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 158, 149(C-5), 146, 139, 137(C-2), 127, 126, 125, 117(CN), 116, 109, 98(C-4). Anal. Calcd for C17H12N4O4: C, 60.71; H, 3.57; N, 16.67. Found: C, 60.55; H, 3.71; N, 16.69. Compound 6g: Yield 98%; mp: 289-291C; IR (Nujol mull) (numax/cm-1): 3355, 3126, 2218, 1633, 1606, 1524, 1501. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.24 (s, 1H, OH), 10,15 (s, 1H, OH), 8.99 (s, 1H, N=CH),9.97 (s, 1H, OH), 8.68 (s, 1H, OH), 8.01 (s, 1H, H-2), 7.32 (d, J=8.7Hz, 2H, ArH), 7.01 (d, J=9.0Hz, 1H, ArH), 6.89 (d, J=8.7Hz, 2H, ArH), 6.45 (d, J=9.0Hz, 1H, ArH). 13C NMR (DMSO-d6, 100MHz): deltaC (ppm) 165(Cimin), 158, 152, 150, 147(C-5), 138(C-2), 132, 127, 125, 124, 117(CN), 116, 112, 109, 99(C-4). Anal. Calcd for C17H12N4O4.1.8H2O: C, 55.37; H, 4.23; N, 15.20. Found: C, 55.10; H, 4.34; N, 15.08. Compound 6h: Yield 86%; mp: 300C (dec.); IR (Nujol mull) (numax/cm-1): 3368, 3302, 3141, 2227, 1652, 1609, 1582, 1568, 1522. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 11.43 (s, 2H, OH), 10.48 (s, 1H, OH), 9.96 (s, 1H, OH), 9.31 (s, 1H, N=CH), 7.96 (s, 1H, H-2), 7.29 (d, J=9.0Hz, 2H, ArH), 6.88 (d, J=9.0Hz, 2H, ArH), 5.79 (s, 2H, ArH). 13C NMR(DMSO-d6, 100MHz): deltaC (ppm) 166(Cimin), 163, 161, 158, 147(C-5), 137(C-2), 127, 125, 117(CN), 116, 102, 98(C-4), 95. Anal. Calcd for C17H12N4O4.0.6H2O: C, 58.82; H, 3.81; N, 16.15. Found: C, 58.74; H, 3.91; N, 16.15. Compound 6i: Yield 42%; mp: 253-255C; IR (Nujol mull) (numax/cm-1): 3475, 3133, 2223, 1608, 1584. 1H NMR (DMSO-d6, 400MHz): deltaH (ppm) 9.70 (br s, 2H, OH), 8.73 (s, 1H, N=CH), 8.05 (s, 1H, H-2),...

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2768 - 2772

32
[ 528-58-5 ]
[ 99-50-3 ]
[ 83-30-7 ]
[ 487-70-7 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 18939 - 18944

33
[ 487-70-7 ]
[ 2760-98-7 ]
[ 1622386-35-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With acetic acid; In methanol;Reflux;	General procedure: A mixture of an appropriate dihydrazide (1 mmol), an appropriate hydroxybenzaldehyde (2 mmol) and acetic acid (2/3 drops) in methanol (25 ml) was heated under reflux with stirring for 6-8 h. Then the reaction mixture was cooled with stirring. Precipitated solid was collected by filtration, and washed with little ethanol and hexane to give the target products 3a-f, 5a-f and 8a-h.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3802 - 3806

34
[ 487-70-7 ]
[ 136-64-1 ]
[ 1622386-30-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With acetic acid; In methanol;Reflux;	General procedure: A mixture of an appropriate dihydrazide (1 mmol), an appropriate hydroxybenzaldehyde (2 mmol) and acetic acid (2/3 drops) in methanol (25 ml) was heated under reflux with stirring for 6-8 h. Then the reaction mixture was cooled with stirring. Precipitated solid was collected by filtration, and washed with little ethanol and hexane to give the target products 3a-f, 5a-f and 8a-h.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3802 - 3806

35
[ 5350-57-2 ]
[ 487-70-7 ]
2,4,6-trihydroxybenzaldehyde N-(diphenylmethylene)hydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With acetic acid; In ethanol;Reflux;	General procedure: Benzophenone hydrazone derivatives 1-25 were synthesized by refluxing a mixture of benzophenone hydrazone (3 mmol) and substituted benzaldehyde (3 mmol) in the presence of HPLC grade ethanol and 1-2 drops of acetic acid for 2-3 h. Completion of reaction was monitored by TLC. After completion of reaction, the crystalline powder of benzophenone hydrazone derivatives were collected and washed with hexane and dried to afford compounds 1-25 in high yields. Recrystallization from methanol afforded pure crystals. The structures of synthetic compounds 1-25 were confirmed by 1H NMR, EI mass spectroscopy, and elemental analysis.

Reference： [1]Medicinal Chemistry,2013,vol. 9,p. 588 - 595
[2]Journal of the Chemical Society of Pakistan,2015,vol. 37,p. 479 - 483
[3]Journal of the Chemical Society of Pakistan,2016,vol. 38,p. 954 - 958

36
[ 487-70-7 ]
[ 107-30-2 ]
[ 1132988-93-2 ]

Yield	Reaction Conditions	Operation in experiment
80%		To a solution of compound 7 (10 g, 64.9 mmol)in CH2Cl2 (200 mL) was added DIPEA (28.3 mL, 162.2 mmol). The resulting mixture was stirredfor 10 mins in an ice-bath under N2. MOMCl (10.8 mL, 142.7 mmol) was added dropwise to thereaction mixture by addition funnel. The reaction mixture was warmed to room temperature (rt) andstirred for 3 h. The mixture was concentrated in vacuo. The residue was diluted with EtOAc (100 mL)and washed with distilled H2O (3 80 mL). The organic layer was dried over Na2SO4, filtered andremoved in vacuo. The residue was purified by silica gel chromatography (EtOAc:n-hexane = 1:9) togive compound 20 (12.3 g, 80%), a light-yellow microcrystalline powder; 1H-NMR (CDCl3, 300 MHz) delta 12.29 (1H, s), 10.16 (1H, s), 6.25 (1H, d, J = 2.1 Hz), 6.23 (1H, d, J = 2.1 Hz), 5.24 (2H, s), 5.18 (2H, s),3.51 (3H, s), 3.47 (3H, s); 13C-NMR (CDCl3, 125 MHz) delta 192.1, 165.6, 165.5, 161.2, 106.9, 96.6, 94.6, 94.1,94.0, 56.6, 56.5; HR-ESI-MS m/z 243.0858 [M + H]+ (calcd. for C11H15O6, 243.0863).
80%		Example 1 Preparation of 2-Hydroxy-4,6-bis(methoxymethoxy)benzaldehyde (Formula 20) To a solution of Formula 7 (10 g, 64.9 mmol) in CH2Cl2 (200 mL) was added DIPEA (28.3 mL, 162.2 mmol). The resulting mixture was stirred for 10 min in an ice-bath under N2. MOMCl (10.8 mL, 142.7 mmol) was added dropwise to the reaction mixture by an addition funnel. The reaction mixture was warmed to room temperature (rt) and stirred for 3 h. The mixture was concentrated in vacuo. The residue was diluted with EtOAc (100 mL) and washed with distilled H2O (3*80 mL). The organic layer was dried over Na2SO4, filtered and removed in vacuo. The residue was purified by silica gel chromatography (EtOAc:n-hexane=1:9) to obtain Formula 20 (12.3 g, 80%), light-yellow microcrystalline powder; 1H-NMR (CDCl3, 300 MHz) delta 12.29 (1H, s), 10.16 (1H, s), 6.25 (1H, d, J=2.1 Hz), 6.23 (1H, d, J=2.1 Hz), 5.24 (2H, s), 5.18 (2H, s), 3.51 (3H, s), 3.47 (3H, s); 13C-NMR (CDCl3, 125 MHz) delta 192.1, 165.6, 165.5, 161.2, 106.9, 96.6, 94.6, 94.1, 94.0, 56.6, 56.5; HR-ESI-MS m/z 243.0858 [M+H]+ (calcd. for C11H15O6, 243.0863).
60%	With triethylamine; In acetonitrile; at 0℃; for 1.33333h;Inert atmosphere;	In argon atmosphere, Et3N (0.57?mL, 4.07?mmol) and MOMCl (4.07?mmol in 5?mL anhydrous acetonitrile) were added dropwise successively to a solution of <strong>[487-70-7]2,4,6-trihydroxybenzaldehyde</strong> (0.30?g, 1.95?mmol) in anhydrous acetonitrile (6?mL) at 0?C. The mixture was stirred at 0?C for 80?min. TLC analysis indicated that the reaction was completed. After quenching the reaction mixture with ice cold water (10?mL), the slurry was extracted with ethyl acetate (5?mL?*?3). The combined organic extracts were washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate?=?10:1) to provide 2-hydroxy-4,6-bis(methoxymethoxy)benzaldehyde (0.28?g, 60%) as a white solid. 1H NMR (300?MHz, DMSO-d6) delta 12.17 (s, 1H), 10.10 (s, 1H), 6.29 (d, J?=?1.8?Hz, 1H), 6.20 (d, J?=?1.8?Hz, 1H), 5.31 (s, 2H), 5.26 (s, 2H), 3.44 (s, 3H), 3.39 (s, 3H). 13C NMR (75?MHz CDCl3) 192.3, 165.8, 161.4, 119.7, 107.1, 96.8, 94.8, 94.3, 94.3, 56.8, 56.6. MS (ESI): m/z 241.1 [M-H]-.

60%

With triethylamine; In acetonitrile; at 0℃; for 1.33333h;Inert atmosphere;

Under Ar protection,Dissolving <strong>[487-70-7]2,4,6-trihydroxybenzaldehyde</strong> (Compound 1-1) (0.30 g, 1.95 mmol) in 6 mL of anhydrous acetonitrile,Triethylamine (0.57 mL, 4.07 mmol) was slowly added dropwise to the reaction solution at 0 C.Keep the temperature constant,Chloromethyl methyl ether (4.07 mmol) in anhydrous acetonitrile was slowly added dropwise to the system. After the addition, the solution was stirred at 0 C for 80 mins.TLC showed that the raw materials were consumed. 15 mL of ice water was added to quench the reaction. The ethyl acetate (5 mL x 3) was used to extract the aqueous phase. The organic phases were combined and the organic phase was washed with saturated brine.Dry over anhydrous sodium sulfate, evaporate the organic phase to obtain the crude product, and subject to flash column chromatography (petroleum ether: ethyl acetate = 10: 1).Compound 1-2 (white solid, 0.28 g) was obtained in a yield of 60%.

Reference： [1]Molecules,2017,vol. 22
[2]Patent: US2019/322637,2019,A1 .Location in patent: Paragraph 0051
[3]Organic Letters,2015,vol. 17,p. 4110 - 4113
[4]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 116 - 124
[5]Patent: CN110272436,2019,A .Location in patent: Paragraph 0093-0095; 0097

37
[ 102-32-9 ]
[ 487-70-7 ]
[ 108-24-7 ]
5,7-diacetoxy-3-(3',4'-diacetoxyphenyl)coumarin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium acetate at 160℃; for 6h; Inert atmosphere;
65%	With sodium acetate at 160℃; for 6h; Inert atmosphere;	General procedure for synthesis of o-diacetoxy-3-phenylchromenones (4a-f) General procedure: A mixture of benzaldehyde (2a-d) (20 mmol), phenylacetic acids (3a-c) (20 mmol), and sodium acetate (50 mmol) was stirred in 40 mL acetic anhydride at 160 °C under N2 atmosphere for 6 h. On reaction completion, the mixture was poured into ice-cold water (200 mL). The crude product was filtered and recrystallized from ethanol.

Reference： [1]Alparslan, Mustafa Muhlis; Daniş, Özkan [Archiv der Pharmazie, 2015, vol. 348, # 9, p. 635 - 642]
[2]Danis, Ozkan; Demir, Serap; Gunduz, Cihan; Alparslan, Mustafa Muhlis; Altun, Selcuk; Yuce-Dursun, Basak [Research on Chemical Intermediates, 2016, vol. 42, # 6, p. 6061 - 6077]

38
[ 5055-39-0 ]
[ 487-70-7 ]
(E)-N'-(2,4,6-trihydroxybenzylidene)-1H-indole-2-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With acetic acid; In methanol; for 3h;Reflux;	General procedure: 1H-Indole-2-carbohydrazones were synthesized by refluxing inmethanol a mixture of 1 mmol each 1H-indole-2-carbohydrazidewith different arylaldehydes catalyzed by acetic acid for 3 h. Theprogress of reaction was monitored by TLC. After completion ofreaction, the solvent was evaporated by vacuum to afford crudeproducts which were further recrystallized in methanol and gotpure product in good to excellent yields.5.2.6 (E)-N'-(2,4,6-trihydroxybenzylidene)-1H-indole-2-carbohydrazide (2) Yield: 85%. m.p. 256-258 C; Brown crystals; UV (MeOH) lambdamax (nm) 346.62; IR (KBr): 3380 cm-1 (OH-str), 3326 cm-1 (2 amine N-H Str), 1642 cm-1 (C=O), 1615 cm-1 (Ar C=C), 1581 cm-1 (N-H Bend), 1259 cm-1 (C-N str), 1160 cm-1 (C-O str). 1H NMR (500 MHz, DMSO-d6): delta 11.97 (s, 1H, NH), 11.77 (s, 1H, NH), 11.14 (s, 1H, OH), 9.92 (s, 2H, 2 * OH), 8.80 (s, 1H, ArCH=N), 7.68 (d, 1H, J = 8.0 Hz, H-4), 7.48 (d, 1H, J = 8.0 Hz, H-7), 7.27 (s, 1H, H-3), 7.24 (t, 1H, J = 7.0 Hz, H-5), 7.09 (t, 1H, J = 7.5 Hz, H-6), 5.86 (s, 2H, H-3', H-5'); 13C NMR (125 MHz, DMSO-d6): delta 163.80, 163.80, 163.20, 157.40, 143.60, 139.60, 138.70, 131.20, 121.60, 120.60, 119.50, 114.60, 111.10, 106.50, 96.20, 96.20; Anal. Calcd. for C16H13N3O4, C = 61.72, H = 4.20, N = 13.51, Found C = 61.71, H = 4.20, N = 13.49; EI MS m/z (% rel. abund.): 311. (M+, 30), 293 (12) 144 (100), 116 (15), 75 (12).
77%	In ethanol; for 18h;Reflux;	General procedure: A mixture of hydrazide 3 (1 mmol) and the appropriate aldehyde(1 mmol) in EtOH (10 mL) was refluxed for 18 h. After cooling theformed precipitate was filtered off and purified by crystallization fromthe adequate solvent to give the hydrazone derivatives.

Reference： [1]Bioorganic Chemistry,2015,vol. 63,p. 24 - 35
[2]Bioorganic Chemistry,2019,vol. 85,p. 568 - 576

39
[ 487-70-7 ]
[ 591-27-5 ]
2-[(3-hydroxyphenyl)imino]methyl}benzene-1,3,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In water; at 25℃; for 2h;	General procedure: Twenty-one (hydroxyphenyliminomethyl)phenols were prepared following the protocoldescribed by Tanaka and Shiraishi [16]. Briefly, equimolar amounts of mono-, di- and tri- hydroxybenzaldehydes (HBA) and 2-, 3- or 4-aminophenols (AP) were stirred (2 h) in distilled water at roomtemperature (25 C). Obtained products were filtered, washed by water and dried at 45 C. Yields of(Hydroxyphenyliminomethyl)phenols ranged between 36%-95%. The prepared compounds werecharacterized by melting point, elemental analysis, 1H- and 13C-NMR, IR and MS spectra.

Reference： [1]Molecules,2016,vol. 21

40
[ 487-70-7 ]
[ 613-94-5 ]
(E)-N'-(2,4,6-trihydroxybenzylidene)benzohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In ethanol; at 40℃;	General procedure: Benzohydrazide (1.0 equiv) and various benzaldehydes (a-m, 1.5 equiv) were dissolved in anhydrous ethanol (5 mL) and stirred at 40 C for overnight. The solvent was removed under vacuum. The product was obtained as yellow solid, which was filtered and washed with ethyl ether. Remained benzaldehyde was washed out by ethyl ether. (Yield; 80-85%).
81%	In ethanol; at 80℃;	General procedure: Compounds 3a-o were prepared as previously described(Alam and Lee 2015b). Briefly, benzohydrazides (2, 10 mM)in 30 cm3 ethanol were added drop-wise into 20 mL ofsuitably substituted benzaldehydes (10 mM) in ethanol. Themixture was stirred and refluxed for 1.5-2.5 h. Reactionprogress was monitored by TLC (Silica gel 60F254, Merck,Germany). After cooling reaction mixtures to ambient temperature,mixtures were filtered to give solid crude products, which were crystallized from ethanol yielding the purecompounds. All compounds except 3a, 3c, 3g, 3h, and 3m-oare new (Alam and Lee 2015b) and their spectral and characterizationdata are included in the supplementary material.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 120,p. 202 - 216
[2]Archives of Pharmacal Research,2016,vol. 39,p. 191 - 201
[3]EXCLI Journal,2016,vol. 15,p. 350 - 361

41
[ 1197-09-7 ]
[ 487-70-7 ]
2,4,6,8-tetrahydroxyxanthylium chloride [ No CAS ]
[ 1154-78-5 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 5%; 65%	With methanol; chloro-trimethyl-silane; In ethyl acetate; at 0℃; for 0.5h;	Equimolar amounts (1 mmol) of <strong>[487-70-7]2,4,6-trihydroxybenzaldehyde</strong> and 3,4-dihydroxyacetophenone were dissolved in 3 mL of AcOEt/MeOH (2/1, v/v). After cooling to 0 C, TMSCl (20 equiv) was added and the solution stirred for 30 min at 0 C. LTN was totally precipitated by adding AcOEt. After filtration, LTN was isolated asa red powder (yield65%). To remove the yellow xanthylium contaminant(ca. 5%), LTN was crystallized in EtOH/AcOEt.

Reference： [1]Tetrahedron,2016,vol. 72,p. 4294 - 4302

42
[ 487-70-7 ]
[ 99-93-4 ]
[ 1151-98-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With methanol; chloro-trimethyl-silane; In ethyl acetate; at 0℃; for 1h;	A solutionof <strong>[487-70-7]2,4,6-trihydroxybenzaldehyde</strong> (1 mmol) and 4-hydroxyacetophenone (2 equiv) in 3 mL of AcOEt/MeOH (2/1, v/v)was cooled to 0 C and TMSCl (20 equiv) was added. After 60 min of stirring, complete precipitation of APN was achieved. Crystallizationin MeOH/AcOEt afforded APN as a red powder. Yield78%

Reference： [1]Tetrahedron,2016,vol. 72,p. 4294 - 4302

43
[ 487-70-7 ]
2,2,4,4-tetramethyl-6-(3-methylbutylidene) cyclohexane-1,3,5-trione [ No CAS ]
2,4,6-trihydroxy-3-(1-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-en-1-yl)-3-methylbutyl)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With sodium hydride; In tetrahydrofuran; mineral oil; at 20℃; for 0.5h;Inert atmosphere;	General procedure: Sodium hydride (30.0 mg, 0.75 mmol, 60% in mineral oil) was carefully added to a solution of acylphloroglucinol 6 (0.5 mmol) in THF (8 mL), then the unsaturated triketone 10 (62.5 mg, 0.25 mmol) in THF (2 mL) was slowly added. The resulting mixture was stirred for 0.5 h at room temperature, and then quenched with 1 N HCl (3 mL) and extracted with EtOAc (3 × 5 mL), washed with brine, and concentrated in vacuum. The crude product was purified by flash chromatography (silica gel, hexane:EtOAc = 10:l to 2:l) to provide derivatives of the general structure 11 with yields ranging from 30% to 80%. The yields and spectra data of 11 were seen in the supporting information.
	With sodium hydride; In tetrahydrofuran; mineral oil; at 20℃; for 0.5h;	Sodium hydride (30.0 mg, 0.75 mmol, 60% mineral oil)Was slowly added to a solution of the acyl phloroglucinolate compound (compound 6) (0.5 mmol) in tetrahydrofuran (5 mL)A solution of compound 10 (unsaturated ketone) (62.5 mg, 0.25 mmol) in tetrahydrofuran (2 mL) was then added.After the mixture was stirred at room temperature for half an hour, 5 mL of 1N aqueous hydrochloric acid was added.The organic phase was separated and the aqueous phase was extracted three times with ethyl acetate (5 mL), washed with saturated brine (5 mL)Dried over anhydrous sodium sulfate, and evaporated to evaporate the remaining organic solvent.The remaining crude product was then separated by silica gel column (n-hexane: ethyl acetate = 10: 1-2: 1)The desired target product 11 can be obtained in a yield of 30-80%.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 492 - 499
[2]Patent: CN105859537,2016,A .Location in patent: Paragraph 0029; 0065-0066
[3]MedChemComm,2018,vol. 9,p. 1698 - 1707

44
[ 487-70-7 ]
[ 110429-45-3 ]
2,4-bis(3,6,9,12-tetraoxatridecyloxy)-6-hydroxybenzaldehyde [ No CAS ]
2,4,6-tris(3,6,9,12-tetraoxatridecyloxy)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 36% 2: 20%	Stage #1: 2,4,6-trihydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 0.5h; Stage #2: 1-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-2-methoxy-ethane In N,N-dimethyl-formamide at 80℃; for 1.5h;

Reference： [1]Liu, Mengran; Chen, Chih-Yuan; Mandal, Amit Kumar; Chandrashaker, Vanampally; Evans-Storms, Rosemary B.; Pitner, J. Bruce; Bocian, David F.; Holten, Dewey; Lindsey, Jonathan S. [New Journal of Chemistry, 2016, vol. 40, # 9, p. 7721 - 7740]

45
[ 109-97-7 ]
[ 487-70-7 ]
[ 110429-45-3 ]
5-[2,4,6-tris(3,6,9,12-tetraoxatridecyloxy)phenyl]dipyrromethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: pyrrole; 2,4,6-trihydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 0.5h; Stage #2: 1-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-2-methoxy-ethane In N,N-dimethyl-formamide at 60 - 80℃; for 16h; Stage #3: pyrrole With indium(III) chloride at 20℃; for 3.5h; Inert atmosphere;

46
[ 67127-78-0 ]
[ 487-70-7 ]
C₁₆H₁₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.2%	With sodium hydroxide; In water;Inert atmosphere; Reflux;	3-Acetyl-2-hydroxybenzoic acid (1.15, 6.36 vis) and 2,4,6-trihydroxybenzaldehyde(0.98 g, 6.36 mmol) was added to a one-necked flask, and 10 ml of a 20% aqueous solution of sodium hydroxide was further added thereto, followed by magnetic stirring. Oil bathWarm to reflux reaction, TLC track to complete the reaction, cooling, the reaction solution poured into 100ml of ice water, adjusted to pH with dilute hydrochloric acid.The organic phase was washed with water (3 X 30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressureCompound 3 was obtained in a yield of 86.2%

Reference： [1]Patent: CN104513216,2016,B .Location in patent: Paragraph 0027; 0028; 0029

47
[ 67127-78-0 ]
[ 487-70-7 ]
C₂₈H₃₂O₁₇ [ No CAS ]

Reference： [1]Patent: CN104513216,2016,B

48
[ 487-70-7 ]
[ 107806-82-6 ]
C₁₆H₁₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.9%	With sodium hydroxide In water Inert atmosphere; Reflux;	11 2-hydroxy-4-acetylbenzoic acid (1.15)and 2,4,6-trihydroxybenzoic acidAldehyde (0.98 g, 6.36 mmol) was added to a one-necked flask, and 10 ml of a 20% aqueous solution of sodium hydroxide was added thereto, followed by magnetic stirring. oil bathThe reaction was warmed to reflux and the reaction was complete by TLC. After cooling, the reaction solution was poured into 100 ml of ice water and adjusted to pH with dilute hydrochloric acid. The organic phase was washed with water (3 X 30 mL), dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressureTo give the compound 11 in a yield of 84.9%.

Reference： [1]Current Patent Assignee: HANGZHOU ADAMERCK PHARMLABS - CN104513216, 2016, B Location in patent: Paragraph 0059; 0060; 0061

49
[ 487-70-7 ]
[ 107806-82-6 ]
C₂₈H₃₂O₁₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide / water / Inert atmosphere; Reflux 2: scandium tris(trifluoromethanesulfonate) / water / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: HANGZHOU ADAMERCK PHARMLABS - CN104513216, 2016, B

50
[ 16357-40-7 ]
[ 487-70-7 ]
C₁₆H₁₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydroxide; In water;Inert atmosphere; Reflux;	<strong>[16357-40-7]3-Acetyl-4-hydroxybenzoic acid</strong> (1.15, 6.36 mmol) and 2,4,6-trihydroxybenzaldehyde(0.98 g, 6.36 mmol) was added to a one-necked flask, and 10 ml of a 20percent aqueous solution of sodium hydroxide was further added thereto, followed by magnetic stirring. The oil bath was heated to reflux and the reaction was followed by TLC. The reaction was cooled and the reaction solution was poured into 100 ml of ice water. The pH was adjusted to pH with dilute hydrochloric acid.The organic phase was washed with water (3 X 30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressureCompound 1 was obtained in a yield of 88percent.

Reference： [1]Patent: CN104513216,2016,B .Location in patent: Paragraph 0019; 0020; 0021

51
[ 16357-40-7 ]
[ 487-70-7 ]
C₂₈H₃₂O₁₇ [ No CAS ]

Reference： [1]Patent: CN104513216,2016,B

52
[ 1197-09-7 ]
[ 487-70-7 ]
[ 1154-78-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With chloro-trimethyl-silane In methanol; ethyl acetate at 0℃; for 1h;

Reference： [1]Cruz, Luís; Sousa, Joana L.C.; Marinho, Andreia; Mateus, Nuno; de Freitas, Victor [Tetrahedron Letters, 2017, vol. 58, # 2, p. 159 - 162] Sousa, Joana L.C.; Gomes, Vânia; Mateus, Nuno; Pina, Fernando; de Freitas, Victor; Cruz, Luís [Tetrahedron, 2017, vol. 73, # 41, p. 6021 - 6030]

53
[ 161942-89-8 ]
[ 487-70-7 ]
3-(4-bromothiophen-2-yl)-5,7-dihydroxycoumarin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium acetate / 16 h / Reflux 2: hydrogenchloride / methanol; water / 3 h / Reflux

Reference： [1]Pintus, Francesca; Matos, Maria J.; Vilar, Santiago; Hripcsak, George; Varela, Carla; Uriarte, Eugenio; Santana, Lourdes; Borges, Fernanda; Medda, Rosaria; Di Petrillo, Amalia; Era, Benedetta; Fais, Antonella [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 5, p. 1687 - 1695]

54
[ 161942-89-8 ]
[ 487-70-7 ]
[ 108-24-7 ]
C₁₇H₁₁BrO₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate for 16h; Reflux;	General procedure for the synthesis of acetoxy-3-arylcoumarins General procedure: Compounds were synthesized under anhydrous conditions,using a material previously dried at 60 C for at least 12 h and at 300 C for a few minutes immediately before use. A solution containinganhydrous CH3CO2K (2.94 mmol), the corresponding arylaceticacid (1.67 mmol) and the correspondinghydroxysalicylaldehyde (1.67 mmol), in Ac2O (1.2 mL), wasrefluxed for 16 h. The reaction mixture was cooled, neutralizedwith 10% aqueous NaHCO3, and extracted with EtOAc(3 30 mL). The organic layers were combined, washed withwater, dried over anhydrous Na2SO4 and the solvent was evaporatedunder reduced pressure. The product was purified by recrystallizationin EtOH and dried in vacuum to afford the desiredcompound.

55
[ 487-70-7 ]
[ 2002-68-8 ]
N-(2,4,6-dihydroxybenzylidene)-N′-[2,6-dinitro-4-(trifluoromethyl)]phenylhydrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With trifluoroacetic acid; In ethanol; at 20℃;Inert atmosphere;	General procedure: A solution of 2,6-dinitro-4(trifluoromethyl)phenylhydrazine 3 (1 mmol) in ethanol (3 mL) was added to a solution of aldehydes4a-4iin ethanol (5 mL) and trifluoroacetic acid (0.5 mL). The reaction mixture was stirred for 3-4 h at room temperature in argon atmosphere and monitored by TLC. The reaction mixture was cooled to 0 C, and the red solid product was filtered off, washed with ethanol/ether (1:5), and dried. The product was purified by column chromatography on silica gel in hexane/ethylacetate (3:1) as the mobile phase.

Reference： [1]Molecules,2017,vol. 22

56
[ 487-70-7 ]
[ 95-54-5 ]
C₁₃H₁₀N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium metabisulfite; In N,N-dimethyl-formamide; at 160℃; for 4h;	The raw materials o-phenylenediamine (216 mg, 2 mmol),2,4,6-hydroxybenzaldehyde (311mg, 2.2mmol) and sodium metabisulfite (190mg, 2mmol) was charged bis mouth bottle,Then, 15 mL of solvent N, N-dimethylformamide was injected,The reaction was stirred at 160 C for 4 hours.Post-processing:After the reaction, the mixture was cooled to room temperature,Add 50 mL of deionized water,Filtration gave a yellow powdery solid.The resulting solid was dissolved in ethyl acetate,Add silica gel spin dry column purification,To obtain 290 mg of a pale yellow powder,Yield 60%.

Reference： [1]Patent: CN106497136,2017,A .Location in patent: Paragraph 0048; 0049; 0050

57
[ 586-89-0 ]
[ 487-70-7 ]
4'-carboxy-5,7-dihydroxy-flavylium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With sulfuric acid; In acetic acid; at 20℃; for 24h;	4-Acetylbenzoic acid 2b (106.7 mg, 0.65 mmol) was added to a solution of <strong>[487-70-7]2,4,6-trihydroxybenzaldehyde</strong> 1 (100.6 mg, 0.65 mmol) in AcOH/H2SO4 (4:1) (5 mL). The reaction mixture was stirred at room temperature for 24 h. The crude reaction was pre-purified on a Buchner funnel loaded with reversed-phase C18 silica gel, eluting with acidified aqueous solutions containing increasing percentages of methanol. Then, the desired compound was purified with acidified aqueous/methanolic solutions 50-60%. After the evaporation of methanol, the fractions were freeze-dried and the compound 3b was obtained as an orange solid (122.1 mg, 59%). 1H NMR (600.13 MHz, MeOD-d4/TFA 90:10), delta (ppm): 9.31 (d, J = 8.9 Hz, 1H, H-4), 8.43 (d, J = 8.7 Hz, 2H, H-2',6'), 8.29 (d, J = 8.7 Hz, 2H, H-3',5'), 8.24 (d, J = 8.9 Hz, 1H, H-3), 7.04 and 6.75 (2d, J = 1.8 Hz, 2H, H-6 and H-8). 13C NMR (125.77 MHz, MeOD-d4/TFA 90:10), delta (ppm): 168.7 (C-2), 166.7 (4'-COOH), 159.8 (C-8a and C-5), 136.0 (C-1'), 132.9 (C-4'), 130.3 (C-3',5'), 128.2 (C-2',6'), 115.8 (C-4a), 110.2 (C-3), 102.4 (C-8 or C-6), 94.8 (C-6 or C-8), C-7 not assigned. LC-DAD/ESI-MS: 3b [M]+ m/z 283, lambdamax 400 nm.

Reference： [1]Tetrahedron,2017,vol. 73,p. 6021 - 6030

58
[ 6373-46-2 ]
[ 487-70-7 ]
(E)-2-(((4-(benzyloxy)phenyl)imino)methyl)benzene-1,3,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	In ethanol at 20℃;	4.6 General procedures for the preparation of compound 1-18 General procedure: The respective salicylaldehyde derivatives (5.0 mmol) wereadded to a solution of compound 3a (5.0 mmol) in ethanol(10 mL). The mixture was stirred under room temperature for 2-5 h then followed by filtration and recrystallization in EtOAc orMeOH to obtain the pure compounds.

Reference： [1]Yang, Hua-Li; Cai, Pei; Liu, Qiao-Hong; Yang, Xue-Lian; Fang, Si-Qiang; Tang, Yan-Wei; Wang, Cheng; Wang, Xiao-Bing; Kong, Ling-Yi [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 21, p. 5917 - 5928]

59
[ 88491-44-5 ]
[ 487-70-7 ]
3-(2-bromo-4-hydroxyphenyl)-5,7-dihydroxycoumarin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine; In acetic anhydride; at 110℃; for 7h;	In a 50 mL round bottom flask,2-Bromo-4-hydroxyphenylacetic acid (25 mmol, 5.78 g) was added,<strong>[487-70-7]2,4,6-trihydroxybenzaldehyde</strong> (25 mmol, 3.85 g),Triethylamine (50 mmol, 5.06 g),Acetic anhydride (10 mL), stirred,Oil bath heated to 110 ,The reaction for 7 hours.After the reaction was completed, the reaction liquid while hot poured into 50mL ice water, stirred, a solid precipitated, suction filtered, the filter cake was washed, the filter cake was collected,After drying to give a light brown solid,Is 3- (2-bromo-4-hydroxyphenyl) -5,7-dihydroxycoumarin,Weight 7.68g, yield 88%.

Reference： [1]Patent: CN106565733,2017,A .Location in patent: Paragraph 0062; 0063; 0068; 0073; 0078; 0083; 0088; 0093

60
4-(3,4-dihydroxyphenyl)but-3-en-2-one [ No CAS ]
[ 487-70-7 ]
2-(3,4-dihydroxystyryl)-5,7-dihydroxy-1-benzopyrylium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With chloro-trimethyl-silane; ethyl acetate; In methanol; at 0 - 20℃;	<strong>[487-70-7]2,4,6-Trihydroxybenzaldehyde</strong> (1, 0.28 mmol) and 3,4-dihydroxystyrylmethylketone(2, 2.80 mmol, 10 equiv) were dissolvedin 3mL of AcOEt/MeOH (2:1, v/v). After cooling to 0 C,TMSCl (20 equiv) was added and the solution stirred for 30 minat 0 C and then at room temperature overnight. The crudeproduct was pre-purified in a Buchner funnel loaded with C18silica gel and eluted with acidified aqueous solution of 20-50 %of MeOH. Product in pure form was achieved by column chromatographyusing C18 silica gel with 40 % of acidified MeOH. Adark pink powder was obtained with 90 % of yield (>99 % puritydetermined by LC/MS). 1H NMR (600.13 MHz, DMSO-d6/TFA9:1): delta = 8.93 (d, J = 8.5 Hz, 1 H, H4), 8.24 (d, J = 15.8 Hz, 1 H,Hbeta), 7.62 (d, J = 8.5 Hz, 1 H, H3), 7.35-7.27 (m, 3 H, Halpha, H6? andH2?), 6.91 (d, J = 8.2 Hz, 1 H, H5?), 6.86 (d, J = 1.6 Hz, 1 H, H6),6.68 (d, J = 1.7 Hz, 1 H, H8). 13C NMR (125.77 MHz, DMSO/TFA9:1): delta = 170.8 (C2), 170.5 (C7), 159.3 (C5 or C8a), 158.4 (C5 orC8a), 152.1 (C3? or C4?), 149.0 (Cbeta), 147.5 (C4), 146.6 (C3? or C4?)126.7 (C1?), 125.1 (C2?), 116.3 (C6?), 114.9 (Calpha), 113.4 (C3), 112.5(C4a), 112.1 (C5?), 102.1 (C8), 95.0 (C6). LC-DAD/ESI-MS: [M]+m/z 297 lambdamax 539 nm.

Reference： [1]Synlett,2018,vol. 29,p. 1390 - 1394

61
[ 6099-90-7 ]
[ 68-12-2 ]
[ 487-70-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With trichlorophosphate; In ethyl acetate; at 20.0℃; for 1.0h;Cooling with ice;	In a 1 L single-necked flask, <strong>[6099-90-7]phloroglucinol dihydrate</strong> (38.6 g, 0.238 mol), DMF (55.03 mL, 0.714 mol), ethyl acetate (450 mL),Phosphorus oxychloride (66.32 mL, 0.714 mol) was slowly added dropwise under ice bath.After the addition, transfer to room temperature for 1 h, filter, wash with ethyl acetate, place the filter cake in a 500 mL single-necked flask, add water (150 mL), protect with nitrogen, warm to reflux and maintain for 10 min, then cool to room temperature and then refrigerate in the refrigerator. 1h,Filter, wash with water, collect the filter cake and dry in vacuo without further purification.A white solid was obtained in 36 g, yield 98%.

Reference： [1]Patent: CN108947787,2018,A .Location in patent: Paragraph 0016

62
[ 113207-59-3 ]
[ 487-70-7 ]
(E)-5′-((2,4,6-trihydroxybenzylidene)amino)spiro[[1,3]dioxolane-2,3′-indolin]-2′-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In ethanol for 8h; Reflux;

Reference： [1]Sonmez, Fatih; Gunesli, Zuhal; Kurt, Belma Zengin; Gazioglu, Isil; Avci, Davut; Kucukislamoglu, Mustafa [Molecular Diversity, 2019, vol. 23, # 4, p. 829 - 844]

63
[ 2518-24-3 ]
[ 487-70-7 ]
C₁₅H₁₀N₂O₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019

64
[ 2518-24-3 ]
[ 487-70-7 ]
4-((2,4,6-trihydroxybenzyl)amino)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019

65
[ 487-70-7 ]
[ 7474-78-4 ]
2-(2,4,6-trihydroxyphenyl)-1H-benzo[d]imidazole-5-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium metabisulfite; In ethanol; water; for 24h;Reflux;	General procedure: To a solution of the appropriate 3,4-diaminobenzene derivative (1ad)(2 mmol) in ethanol (15 mL) 2.85 N aqueous solution of sodium metabisulphite (1.6 mL) and the appropriate substituted arylaldehyde(2 mmol) were added. The reaction mixture was heated at reflux for 24 h. The solvent was then evaporated under reduced pressure. The residue was added with HCl 1 N (10 mL), the formed precipitate was filtered off, washed with water (3×10 mL) and purified by crystallization from the adequate solvent to give the title compounds.Following the general procedure benzimidazoles 3 [19], 4 [20], 5 [21],7 [24], 6, 32 and 33 [15] were prepared and their analytical and spectral data are in agreement with those reported in literature.

Reference： [1]Bioorganic Chemistry,2019

66
[ 487-70-7 ]
[ 2632-10-2 ]
(3,4-dichlorophenyl)(4,6-dihydroxybenzofuran-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate In acetonitrile at 20℃;	4.2. General procedure for the synthesis of compounds 1-30 General procedure: In an oven dried round-bottomed flask, a mixture of substitutedsalicylaldehyde (1 mmol), phenacyl bromide derivatives (1 mmol) andK2CO3 (1 mmol) in acetonitrile (10 mL) were stirred at room temperaturefor 4-5 h. After completion of the reaction, the mixture waspoured onto ice resulting in precipitate. Precipitate were filtered andwashed thoroughly with excess distilled water and hexane to affordpure products. The solids were crystallized from ethanol. The overallreaction was monitored through TLC analysis. Compounds 1-30(Table 1) were characterized by different spectroscopic techniques including1H-, 13C NMR, EI-MS, HREI-MS, and IR.

Reference： [1]Ali, Basharat; Ali, Irfan; Chigurupati, Sridevi; Iqbal, Muhammad Shahid; Ji, Xingyue; Khan, Khalid Mohammed; Perveen, Shahnaz; Rafique, Rafaila; Rehman, Ashfaq Ur; Salar, Uzma; Taha, Muhammad; Wadood, Abdul [Bioorganic Chemistry, 2020, vol. 104]

67
[ 487-70-7 ]
[ 2124-31-4 ]
5,7-dihydroxy-4'-dimethylaminoflavylium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hexafluorophosphoric acid In acetic acid at 20℃; for 46h;	5,7OH₂4'NMe₂ 5,7OH24'NMe2 was formed from the reaction 2,4,6-trihydroxybenzaldehyde (1.3x10-3 mol, 200 mg) and 4'-dimethylaminoacetophenone (1.3x10-3 mol, 211.8 mg) in 2.596 mL (2 mL/1 mmol) of acetic acid and 0.650 mL of hexafluorophosphoric acid (0.5 mL/1 mmol). The reaction mixture was left at room temperature, during 46 h, under stirring. 5,7OH24'NMe2 was precipitated with diethyl ether, and then the blue dye was purified on LiChroprep RP-18 (40-63 μm, Merck, Germany) column chromatography, being the new compound recovered with 30% (v/v) of methanol acidified with 2% HCl. The methanol was removed in a rotary evaporator under vacuum at 38 °C and the water fraction was frozen at -18 °C and freeze-dried. The reaction yield was 23%.

Reference： [1]Araújo, Paula; Rita Pereira, Ana; de Freitas, Victor; Mateus, Nuno; Fernandes, Iva; Oliveira, Joana [Tetrahedron Letters, 2021, vol. 85]

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[ 487-70-7 ] Synthesis Path-Upstream 1~18

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