[ CAS No. 88-03-9 ] {[proInfo.proName]}

Name: 88-03-9|2-Methylbenzene-1,3,5-triol|97%
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Quality Control of [ 88-03-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 88-03-9 ]

Product Details of [ 88-03-9 ]

CAS No. :	88-03-9	MDL No. :	MFCD00016458
Formula :	C₇H₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BPHYZRNTQNPLFI-UHFFFAOYSA-N
M.W :	140.14	Pubchem ID :	66606
Synonyms :

Calculated chemistry of [ 88-03-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	3.0
Molar Refractivity :	37.48
TPSA :	60.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.01
Log Po/w (XLOGP3) :	1.22
Log Po/w (WLOGP) :	1.11
Log Po/w (MLOGP) :	0.53
Log Po/w (SILICOS-IT) :	0.85
Consensus Log Po/w :	0.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.92
Solubility :	1.68 mg/ml ; 0.012 mol/l
Class :	Very soluble
Log S (Ali) :	-2.09
Solubility :	1.13 mg/ml ; 0.0081 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.03
Solubility :	13.0 mg/ml ; 0.0929 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 88-03-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 88-03-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 88-03-9 ]

[ 88-03-9 ] Synthesis Path-Downstream 1~49

1
[ 74-90-8 ]
[ 88-03-9 ]
[ 55743-13-0 ]

Reference： [1]Monatshefte fur Chemie,1903,vol. 24,p. 878

2
[ 74-90-8 ]
[ 88-03-9 ]
[ 55743-13-0 ]
[ 854656-95-4 ]

Reference： [1]Chemische Berichte,1942,vol. 75,p. 29,31

3
[ 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

4
[ 88-03-9 ]
[ 141-97-9 ]
[ 103986-38-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogenchloride; In acetic acid; at 25℃; for 0.25h;	Anhydrous HCl was passed through a mixture of MPG (5 g, 36 mmol) and ethyl acetoacetate (3.5 mL, 27 mmol) in glacial AcOH (30 mL) over 15 min at room temperature. A bright yellow precipitate formed was filtered off on a Schott funnel (16 m). The precipitate was washed with some AcOH and dried in a vacuum desiccator at 25 C for 24 h, then recrystallized from MeOH to obtain the product (4.45 g, 80%) as a white powder. M.p. 285-287 C (decomp.), Rf 0.48 (EtOH-benzene (1 : 5)). UV (EtOH), max/nm (lg epsilon): 264.05 (4.07); 327.75 (4.22). 1H NMR (DMSO-d6), delta: 2.00 (s, 3 H, Me(8)); 2.47 (d, 3 H, Me(4), 4JH,H = 1.1 Hz); 5.54 (q, 1 H, H(3), 4JH,H = 1.1 Hz); 6.36 (s, 1 H, H(6)); 10.19 (s, 1 H, 7OH); 10.22 (s, 1 H, 5OH). 13C NMR, delta: 7.8 (dd, Me(8)); 23.7 (dd, Me(4)); 98.6 (d, C(6)); 102.0 (br.sext, C(8)); 102.1 (m, C(4a)); 108.4 (dq, C(3)); 154.0 (br.q,C(8a)); 155.22 (t, C(5)); 155.26 (qd, C(4)); 159.0 (br.sext, C(7)); 160.3 (d, C(2)). IR (KBr), nu/cm-1: 826, 1096 (delta(CHAr)); 1221 (nu(CO)); 1609 (nu(C-CAr)); 1654 (nu(C=O)); 2931 br (nuas,s(Me), nu(CHAr)); 3216 (nu(OH)). MS (EI, 10 eV), m/z (Irel (%)): 206 [M]+(50), 178 [M - CO]+ (80), 29 [HCO]+ (100), 39 (90).Found (%): C, 64.02; H, 4.81. C11H10O4. Calculated (%): C, 64.07; H, 4.89.

Reference： [1]Russian Chemical Bulletin,2015,vol. 64,p. 154 - 160
Izv. Akad. Nauk, Ser. Khim.,2015,p. 154 - 160
[2]Journal of the Chemical Society,1954,p. 4565,4570

5
[ 88-03-9 ]
[ 75-36-5 ]
[ 2657-28-5 ]

Reference： [1]Molecules,2018,vol. 23
[2]Justus Liebigs Annalen der Chemie,1938,vol. 535,p. 149,170
Justus Liebigs Annalen der Chemie,1939,vol. 541,p. 53,66 Anm. 1
[3]ACS Infectious Diseases,2019,vol. 5,p. 1087 - 1104

6
[ 88-03-9 ]
[ 79-30-1 ]
[ 69480-03-1 ]

Reference： [1]Organic and biomolecular chemistry,2020,vol. 18,p. 1135 - 1139
[2]Patent: DE941372,1954,
[3]ACS Infectious Diseases,2019,vol. 5,p. 1087 - 1104

7
[ 88-03-9 ]
[ 141-75-3 ]
[ 1509-06-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With aluminum (III) chloride; In 1,2-dichloro-ethane; at 50℃; for 1h;	Add AlCl3 (14.96 mmol) to 1,2-dichloroethane (6 mL), add butyryl chloride (7.48 mmol) under stirring at room temperature, add intermediate 2 (6.8 mmol) after 10 min, react at 50 C, stop reaction after 1 h. , cooled, poured into dilute hydrochloric acid containing ice, stirred for 5 min, extracted with ethyl acetate, concentrated under reduced pressure, silica gel column chromatography (DCM / MeOH = 100:1) to give pale yellow solid 3, yield: 85% ,
77%		In a 250 mL single-necked flask, intermediate 2 (5 g, 0.036 mol), nitrobenzene (40 mL) was added, and anhydrous aluminum trichloride (19.03 g, 0.142 mol) was added in three portions and stirred for 30 min. After the addition of butyryl chloride (4.08 ml, 0.039 mol), nitrogen protection, reaction at 65 C for 24 h.The reaction solution was poured into 150 mL of ice water, extracted with ethyl acetate, and the organic layer was extracted with a 2 mol/L aqueous sodium hydroxide solution. The aqueous layer was acidified with concentrated hydrochloric acid, extracted with ethyl acetate, washed with saturated brine and evaporated. Solvent,The petroleum ether/ethyl acetate mixed solvent (4:1, v/v) 50 mL was recrystallized to give 5.8 g of a white solid, yield 77%.
77%		In a 250 mL single-necked flask, intermediate 5 (5 g, 0.036 mol), nitrobenzene (40 mL) was added, and anhydrous aluminum trichloride (19.03 g, 0.142 mol) was added in three portions and stirred for 30 min. After addition of butyryl chloride (4.08 ml, 0.039 mol),Nitrogen protection, reaction at 65 C for 24 h. The reaction solution was poured into 150 mL of ice water, extracted with ethyl acetate, and the organic layer was extracted with a 2 mol/L aqueous sodium hydroxide solution. The aqueous layer was acidified with concentrated hydrochloric acid, extracted with ethyl acetate, washed with saturated brine and evaporated. Solvent,Recrystallization of petroleum ether/ethyl acetate mixed solvent (4:1, v/v) 50 mL yielded 5.8 g of white solid, yield 77%

68%

<strong>[88-03-9]2,4,6-trihydroxytoluene</strong> (2 g, 14.28 mmol) was placed in a 250 mL three-necked flask,carbon disulfide (10 mL) and anhydrous aluminum trichloride powder (5.7 g, 42.84 mmol) were added,and nitrobenzene (6 mL) was added with stirring, and heated to reflux. After 0.5 h, then butyrylchloride (1.68 g, 15.7 mmol) was slowly added dropwise, and the mixture was reuxed for 1.5 h, cooledto room temperature, and poured into a mixture of ice water (10 mL of concentrated hydrochloric acid,70 g of ice water) with stirring, and distilled for 30 min. The mixture was filtered while hot, and theyellow needle-like crystals were precipitated in the filtrate. After sufficient cooling, the mixture wasfiltered, and the remaining oil was repeatedly subjected to hot extraction several times. The combinedcrystals were dried to obtain 2-methyl-6-butyrylphloroglucol.

Reference： [1]Patent: CN109293493,2019,A .Location in patent: Paragraph 0270; 0271; 0276; 0277
[2]Patent: CN108947787,2018,A .Location in patent: Paragraph 0018
[3]Patent: CN108997099,2018,A .Location in patent: Paragraph 0009; 0024
[4]Molecules,2018,vol. 23
[5]Justus Liebigs Annalen der Chemie,1954,vol. 585,p. 38,40
[6]ACS Infectious Diseases,2019,vol. 5,p. 1087 - 1104

8
[ 88-03-9 ]
[ 90-02-8 ]
1,3-dihydroxy-2-methylxanthenium bisulfate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 717 - 723

9
[ 88-03-9 ]
[ 645-45-4 ]
[ 70155-33-8 ]

Reference： [1]Journal of Natural Products,2020,vol. 83,p. 3 - 7
[2]Phytochemistry,1978,vol. 17,p. 2015 - 2019

10
[ 88-03-9 ]
[ 108-12-3 ]
[ 49583-27-9 ]

Reference： [1]Phytochemistry,1998,vol. 49,p. 1699 - 1704
[2]ACS Infectious Diseases,2019,vol. 5,p. 1087 - 1104

11
rottlerin [ No CAS ]
[ 88-03-9 ]

Reference： [1]Archiv der Pharmazie,1907,vol. 245,p. 578
[2]Archiv der Pharmazie,1907,vol. 245,p. 578
[3]Archiv der Pharmazie,1906,vol. 244,p. 449

12
[ 7647-01-0 ]
[ 60-29-7 ]
[ 74-90-8 ]
[ 88-03-9 ]
[ 55743-13-0 ]
[ 854656-95-4 ]

Reference： [1]Chemische Berichte,1942,vol. 75,p. 29,31

13
[ 100-97-0 ]
[ 88-03-9 ]
[ 854656-95-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 1750 - 1760
[2]Australian Journal of Chemistry,2005,vol. 58,p. 551 - 555

14
[ 88-03-9 ]
[ 108-24-7 ]
[ 2657-28-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With boron trifluoride diethyl etherate; In acetic acid; at 100℃; for 3h;Inert atmosphere;	To a solution of 17 (1.4 g, 10 mmol) in acetic acid was added acetic anhydride (1.1 ml, 12 mmol) and boron trifluoride diethyl etherate (1.5 ml, 12 mmol) and the reaction was refluxed for 3 h. When it cooled down, acetic acid was removed and ethyl acetate was added to dilute. The organic solution was 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, 10:1) to yield 4 (1.17 g, 65%) as a light yellow crystal. 1H NMR (400 MHz, DMSO) delta 13.90 (s, 1H), 10.76 (s, 1H), 10.51 (s, 1H), 5.96 (s, 1H), 2.52 (s, 3H), 1.81 (s, 3H). 13C NMR (126 MHz, DMSO) delta 203.3, 163.6, 163.0, 160.4, 104.3, 102.0, 94.4, 32.8, 7.6.

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 8263 - 8266
[2]Tetrahedron Letters,2016,vol. 57,p. 1856 - 1859
[3]ChemMedChem,2020
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5415 - 5419

15
[ 108-73-6 ]
[ 88-03-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 1750 - 1760
[2]Australian Journal of Chemistry,2005,vol. 58,p. 551 - 555
[3]Chemische Berichte,1942,vol. 75,p. 29,31
[4]Justus Liebigs Annalen der Chemie,1903,vol. 329,p. 278
[5]Justus Liebigs Annalen der Chemie,1903,vol. 329,p. 278
[6]Tetrahedron Letters,2016,vol. 57,p. 1856 - 1859
[7]Molecules,2018,vol. 23
[8]Patent: CN108997099,2018,A
[9]Patent: CN109293493,2019,A
[10]ACS Infectious Diseases,2019,vol. 5,p. 1087 - 1104
[11]Organic and biomolecular chemistry,2020,vol. 18,p. 1135 - 1139

16
[ 88-03-9 ]
[ 789493-47-6 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 1059,1065

17
[ 88-03-9 ]
[ 1454-53-1 ]
3-Benzyl-8,10-dihydroxy-9-methyl-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%		EXAMPLE 8 3-Benzyl-8,10-dihydroxy-9-methyl-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one hydrochloride Prepared by the procedure of Example 1 from 3,5-dihydroxy-4-methylphenol and ethyl 1-benzyl-4-oxo-3-piperidinecarboxylate hydrochloride. The crude product was converted to the hydrochloride salt. Yield 24%; mp 293-299 C.

Reference： [1]Patent: US5760050,1998,A

18
[ 88-03-9 ]
[ 74-88-4 ]
5-methoxy-2,2,4,6,6-pentamethyl-cyclohex-4-ene-1,3-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2383 - 2385

19
[ 88-03-9 ]
C₁₆H₁₈Br₂O₃ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4110 - 4113

20
[ 88-03-9 ]
C₁₆H₁₈ClNO₄ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4110 - 4113

21
[ 88-03-9 ]
3-(4,6-bis(allyloxy)-2-methoxy-3-methylphenyl)-N,N-dimethylpropiolamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4110 - 4113

22
[ 88-03-9 ]
4,6-bis(allyloxy)-2-methoxy-3-methylbenzaldehyde [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4110 - 4113

23
[ 88-03-9 ]
[ 68-12-2 ]
[ 55743-13-0 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4110 - 4113
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 14650 - 14653
Angew. Chem.,2018,vol. 130,p. 14861 - 14864,4

24
[ 88-03-9 ]
[ 108-24-7 ]
[ 64-19-7 ]
[ 2657-28-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With boron trifluoride diethyl etherate; at 100℃; for 5h;	Toa solution of trihydroxytoluene 3 (1.54g, 10 mmol) in HOAc (30.0 mL) and Ac2O (3.0 mL) at room temperature, then BF3·OEt2 (1.7 mL, 13 mmol) was added. The mixture was heated at 100 C for 5 h. The mixture was adjusted to pH 4 by 2 N NaOH at 0 C then the mixture was extracted with EtOAc and 5% MeOH/EtOAc. The combined organic phases were concentrated. The residue was dissolved in MeOH (30 mL) and 2 N NaOH (30 mL). After stirring at room temperature for 12 h, the mixture was adjusted to pH 4 by 3 N HCl at 0 C, then the volatile solvent was removed in vacuo. The residue was extracted with EtOAc, washed with water, brine, dried over Na2SO4 and concentrated under vacuum. The residue was chromatographed on silica gel with petroleum ether-EtOAc (3:1 to 1:2 v/v) to provide 4 (1.24 g, 68%),colorless prisms. Compound was characterized by comparing its data with literature values.[2]

Reference： [1]Synthetic Communications,2014,vol. 44,p. 3139 - 3147

25
[ 88-03-9 ]
[ 350-46-9 ]
2,4,6-tris(4-nitrophenoxy)toluene [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2015,vol. 64,p. 473 - 474
Izv. Akad. Nauk, Ser. Khim.,2015,vol. 64,p. 473 - 474,2

26
[ 88-03-9 ]
[ 4468-48-8 ]
2-imino-4,8-dimethyl-3-phenyl-2H-chromene-5,7-diol hydrosulfate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sulfuric acid; acetic acid; at 20℃; for 24h;	General procedure: Methylphloroglucinol 1 (5 g, 36 mmol) was dissolved in amixture of 45 mL of AcOH and 20 mL of H2SO4. Atvigorous stirring aryl-substituted beta-ketonitrile (36 mmol)was added by portions to the solution, the stirring atroom temperature was continued till completedissolution, and the reaction mixture was left standingfor 24 h. The separated dark yellow precipitate wasfiltered off using glass fritted funnel, porosity 16 mum,washed with a little AcOH, dried at 25 in a vacuumdesiccator for 24 h, and recrystallized from EtOH.2-Imino-4,8-dimethyl-3-phenyl-2-chromene-5,7-diol, hydrosulfate (4). Yield 7.01 g (69%),yellow powder, mp 310, Rf 0.11. 1H NMR spectrum,delta, ppm: 2.15 s (3H, 8-CH3), 2.36 s (3H, 4-CH3), 6.93 s(1H, H6), 7.34 d (2H, o, J 7.2 Hz), 7.50 t (1H, p, J7.2 Hz), 7.56 t (2H, m, J 7.2 Hz), 9.76, 11.24 br (5-OH, 7-OH). 13 NMR spectrum, delta, ppm: 7.4 (8-CH3),21.2 (4-CH3), 100.7 (C6), 102.3 (C8), 103.3 (C4a),114.9 (C3), 129.0 (p), 129.5 (m), 130.5 (o), 131.8(i), 150.2 (C8a), 156.5 (C4), 156.8 (C5), 161.3 (C7),164.0 (C2). Mass spectrum, m/z (Irel, %): 280 [M]+(100), 254 (20). Found, %: 53.71; 4.55; N 3.67; S8.47. 1717NO7S. Calculated, %: 53.82; 4.52; N3.69; S 8.45. M 379.38.

Reference： [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 1572 - 1577
Zh. Org. Khim.,2015,vol. 51,p. 1603 - 1608,6

27
[ 88-03-9 ]
[ 63895-78-3 ]
2-imino-4,8-dimethyl-3-(4-methoxyphenyl)-2H-chromene-5,7-diol hydrosulfate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With sulfuric acid; acetic acid; at 20℃; for 24h;	General procedure: Methylphloroglucinol 1 (5 g, 36 mmol) was dissolved in amixture of 45 mL of AcOH and 20 mL of H2SO4. Atvigorous stirring aryl-substituted beta-ketonitrile (36 mmol)was added by portions to the solution, the stirring atroom temperature was continued till completedissolution, and the reaction mixture was left standingfor 24 h. The separated dark yellow precipitate wasfiltered off using glass fritted funnel, porosity 16 mum,washed with a little AcOH, dried at 25 in a vacuumdesiccator for 24 h, and recrystallized from EtOH.

Reference： [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 1572 - 1577
Zh. Org. Khim.,2015,vol. 51,p. 1603 - 1608,6

28
[ 88-03-9 ]
[ 18133-46-5 ]
2-imino-4,8-dimethyl-3-(3,4-dimethoxyphenyl)-2H-chromene-5,7-diol hydrosulfate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With sulfuric acid; acetic acid; at 20℃; for 24h;	General procedure: Methylphloroglucinol 1 (5 g, 36 mmol) was dissolved in amixture of 45 mL of AcOH and 20 mL of H2SO4. Atvigorous stirring aryl-substituted beta-ketonitrile (36 mmol)was added by portions to the solution, the stirring atroom temperature was continued till completedissolution, and the reaction mixture was left standingfor 24 h. The separated dark yellow precipitate wasfiltered off using glass fritted funnel, porosity 16 mum,washed with a little AcOH, dried at 25 in a vacuumdesiccator for 24 h, and recrystallized from EtOH.

Reference： [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 1572 - 1577
Zh. Org. Khim.,2015,vol. 51,p. 1603 - 1608,6

29
[ 88-03-9 ]
[ 91-56-5 ]
1,3-dihydroxy-2-methylacridine-9-carboxylic acid [ No CAS ]