Home Cart 0 Sign in  
X

[ CAS No. 148-53-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 148-53-8
Chemical Structure| 148-53-8
Chemical Structure| 148-53-8
Structure of 148-53-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 148-53-8 ]

Related Doc. of [ 148-53-8 ]

Alternatived Products of [ 148-53-8 ]

Product Details of [ 148-53-8 ]

CAS No. :148-53-8 MDL No. :MFCD00003322
Formula : C8H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :JJVNINGBHGBWJH-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :8991
Synonyms :
3-Methoxysalicylaldehyde
Chemical Name :2-Hydroxy-3-methoxybenzaldehyde

Calculated chemistry of [ 148-53-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.34
TPSA : 46.53 Ų

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 : No
Log Kp (skin permeation) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.6
Log Po/w (XLOGP3) : 1.37
Log Po/w (WLOGP) : 1.21
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : 1.49
Consensus Log Po/w : 1.24

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 : 1.84 mg/ml ; 0.0121 mol/l
Class : Very soluble
Log S (Ali) : -1.95
Solubility : 1.71 mg/ml ; 0.0112 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.88
Solubility : 2.0 mg/ml ; 0.0132 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.16

Safety of [ 148-53-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 148-53-8 ]

* 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 [ 148-53-8 ]
  • Downstream synthetic route of [ 148-53-8 ]

[ 148-53-8 ] Synthesis Path-Upstream   1~51

  • 1
  • [ 148-53-8 ]
  • [ 1668-84-4 ]
Reference: [1] Agricultural and Biological Chemistry, 1980, vol. 44, # 2, p. 235 - 243
  • 2
  • [ 148-53-8 ]
  • [ 7168-85-6 ]
Reference: [1] Helvetica Chimica Acta, 1935, vol. 18, p. 816,826
[2] Chemical and Pharmaceutical Bulletin, 2013, vol. 61, # 10, p. 997 - 1001
[3] Patent: CN106588842, 2017, A,
  • 3
  • [ 148-53-8 ]
  • [ 5768-39-8 ]
Reference: [1] Agricultural and Biological Chemistry, 1980, vol. 44, # 2, p. 235 - 243
  • 4
  • [ 148-53-8 ]
  • [ 105-39-5 ]
  • [ 4790-79-8 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 2001, vol. 51, # 2, p. 156 - 162
[2] Journal of Medicinal Chemistry, 1987, vol. 30, # 1, p. 62 - 67
[3] Patent: WO2004/41275, 2004, A1, . Location in patent: Page/Page column 27
  • 5
  • [ 148-53-8 ]
  • [ 685-87-0 ]
  • [ 4790-79-8 ]
Reference: [1] Patent: EP1270577, 2003, A1,
[2] Patent: US6235771, 2001, B1,
  • 6
  • [ 148-53-8 ]
  • [ 4790-79-8 ]
Reference: [1] Journal of Enzyme Inhibition and Medicinal Chemistry, 2018, vol. 33, # 1, p. 1212 - 1224
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 21, p. 6242 - 6246[3] Angew. Chem., 2018, vol. 130, p. 6350 - 6354,5
  • 7
  • [ 148-53-8 ]
  • [ 105-39-5 ]
  • [ 4790-79-8 ]
  • [ 50551-58-1 ]
Reference: [1] Chemical Biology and Drug Design, 2018, vol. 92, # 2, p. 1497 - 1503
  • 8
  • [ 148-53-8 ]
  • [ 105-36-2 ]
  • [ 4790-79-8 ]
Reference: [1] Helvetica Chimica Acta, 1935, vol. 18, p. 816,826
  • 9
  • [ 2591-86-8 ]
  • [ 217813-03-1 ]
  • [ 32040-06-5 ]
  • [ 148-53-8 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With tetrabutyl ammonium fluoride In acetonitrile at 20℃; for 3 h; Inert atmosphere
Stage #2: at 20℃;
General procedure: To a solution of 3-methoxy-2-(trimethylsilyl)phenyl triflate 1 (53 μL, 0.20 mmol) and 1-formylpiperidine 4, N,N-dibenzylformamide 6, or N-methylformamide 8 (2.0 mmol) in CH3CN (1.4 mL) was added TBAF (1.0 M solution in CH3CN, 0.60 mL, 0.60 mmol) under argon atmosphere at room temperature. After being stirred at the same temperature for 3 h, H2O (0.1 mL) was added to the reaction mixture. The reaction mixture was concentrated under reduced pressure. Purification of the residue by flash silica gel column chromatography (AcOEt/hexane=1/20 to 1/8 with 2percent CH2Cl2) afforded the products 2, 5, 7, and 9.
Reference: [1] Tetrahedron, 2012, vol. 68, # 1, p. 179 - 189
  • 10
  • [ 24677-78-9 ]
  • [ 74-88-4 ]
  • [ 148-53-8 ]
YieldReaction ConditionsOperation in experiment
46% With potassium carbonate In acetone at 20℃; for 12 h; General procedure: Anhydrous potassium carbonate (2 g) and ethyl iodide (0.5 ml) were added to 2,4-dihydroxy benzaldehyde (0.7 g, 5 mmol) acetone (30 ml) and the contents stirred for 12 h at room temperature. After the completion of the reaction as indicated by TLC, the mixture concentrated in vacuo and re-dissolved in benzene (3 × 10 ml). The organic layer concentrated and the residue chromatography on silica gel (60–120 mesh) using n-hexane: ethyl acetate mixture (46:4) as eluent to give JA-2 a crystallized solid (0.75 g, 45percent) 2.2.1.7
Preparation of 2-hydroxy-3-methoxybenzaldehyde
The title compound was prepared from 2,3-dihydroxy benzaldehyde (1.0 g, >7 mmol) and methyl iodide (0.5 ml, 7 mmol) by the method as described for 2-hydroxy-4-ethoxy-benzaldehyde to furnish a semisolid (0.48 g, 46percent) analyzed for C8H8O3. IR (KBr Pellet): 3184, 2932, 1668, 1634, 1578, 1498, 1454, 1428, 1374, 1336, 1292, 1260, 1216, 1170, 1114, 998, 926 cm-1. 1H NMR (200 MHz, CDCl3): δ3.87 (3H, s, OMe), 6.92(1H, dd, J = 7.92 & 7.88 Hz, Ar-H), 7.08(1H, d, J = 7.92 Hz, Ar-H),7.14 (1H, d, J = 7.83 Hz, Ar-H),9.87(1H, s, Ar-CHO), 11.07(1H, s, OH). MS M+ m/z (percent) 152(18), 137(8), 121(15), 81(8), 53(100).
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 114, p. 209 - 219
  • 11
  • [ 67-66-3 ]
  • [ 90-05-1 ]
  • [ 148-53-8 ]
  • [ 121-33-5 ]
YieldReaction ConditionsOperation in experiment
10 %Chromat. With sodium hydroxide In water at 20℃; for 24 h; Inert atmosphere To an aqueous solution of NaOH (20 wtpercent, 20 mL) wereadded guaiacol (5 mmol, 0.62 g) and zeolite (5 g) under N2atmosphere at room temperature. Then chloroform(20 mL) was dropped to the mixture. Dodecane (1 mmol,0.224 mL) was added as GC internal standard. The reactionmixture was stirred at room temperature for 24 h. Thereaction was quenched with 3 N aqueous HCl. The mixturewas extracted with ethyl acetate. The yield and selectivityof products was detected by GC.
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 1287
[2] Chemische Berichte, 1881, vol. 14, p. 2021
[3] Catalysis Letters, 2015, vol. 145, # 2, p. 712 - 714
[4] Catalysis Letters, 2015, vol. 145, # 2, p. 712 - 714
  • 12
  • [ 86-51-1 ]
  • [ 148-53-8 ]
Reference: [1] Synthesis, 1989, # 4, p. 287 - 289
[2] Journal of Chemical Research, 2010, # 4, p. 222 - 227
[3] Chemistry Letters, 2000, # 7, p. 738 - 739
[4] Organic and Biomolecular Chemistry, 2009, vol. 7, # 24, p. 5084 - 5090
[5] Synthetic Communications, 1988, vol. 18, # 2, p. 191 - 196
  • 13
  • [ 68-12-2 ]
  • [ 217813-03-1 ]
  • [ 148-53-8 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: at 20℃; for 3 h; Inert atmosphere
To a solution of TBAF, CsF, TBAHF2, TBAT or TBAF*3H2O (0.60 mmol) in DMF (1.2 mL) was added a solution of 3-methoxy-2-(trimethylsilyl)phenyl triflate 1 (53 μL, 0.20 mmol) in DMF (0.8 mL) under argon atmosphere at room temperature. After being stirred at the same temperature for 3 h, H2O (0.1 mL) was added to the reaction mixture. The reaction mixture was concentrated under reduced pressure. Purification of the residue by flash silica gel column chromatography (AcOEt/hexane=1/20 to 1/8 with 2percent CH2Cl2) afforded the product 2.
Reference: [1] Tetrahedron, 2012, vol. 68, # 1, p. 179 - 189
  • 14
  • [ 5464-77-7 ]
  • [ 217813-03-1 ]
  • [ 56511-50-3 ]
  • [ 148-53-8 ]
YieldReaction ConditionsOperation in experiment
34%
Stage #1: With tetrabutyl ammonium fluoride In acetonitrile at 20℃; for 3 h; Inert atmosphere
Stage #2: at 20℃;
General procedure: To a solution of 3-methoxy-2-(trimethylsilyl)phenyl triflate 1 (53 μL, 0.20 mmol) and 1-formylpiperidine 4, N,N-dibenzylformamide 6, or N-methylformamide 8 (2.0 mmol) in CH3CN (1.4 mL) was added TBAF (1.0 M solution in CH3CN, 0.60 mL, 0.60 mmol) under argon atmosphere at room temperature. After being stirred at the same temperature for 3 h, H2O (0.1 mL) was added to the reaction mixture. The reaction mixture was concentrated under reduced pressure. Purification of the residue by flash silica gel column chromatography (AcOEt/hexane=1/20 to 1/8 with 2percent CH2Cl2) afforded the products 2, 5, 7, and 9.
Reference: [1] Tetrahedron, 2012, vol. 68, # 1, p. 179 - 189
  • 15
  • [ 123-39-7 ]
  • [ 217813-03-1 ]
  • [ 150-19-6 ]
  • [ 148-53-8 ]
YieldReaction ConditionsOperation in experiment
4%
Stage #1: With tetrabutyl ammonium fluoride In acetonitrile at 20℃; for 3 h; Inert atmosphere
Stage #2: at 20℃;
General procedure: To a solution of 3-methoxy-2-(trimethylsilyl)phenyl triflate 1 (53 μL, 0.20 mmol) and 1-formylpiperidine 4, N,N-dibenzylformamide 6, or N-methylformamide 8 (2.0 mmol) in CH3CN (1.4 mL) was added TBAF (1.0 M solution in CH3CN, 0.60 mL, 0.60 mmol) under argon atmosphere at room temperature. After being stirred at the same temperature for 3 h, H2O (0.1 mL) was added to the reaction mixture. The reaction mixture was concentrated under reduced pressure. Purification of the residue by flash silica gel column chromatography (AcOEt/hexane=1/20 to 1/8 with 2percent CH2Cl2) afforded the products 2, 5, 7, and 9.
Reference: [1] Tetrahedron, 2012, vol. 68, # 1, p. 179 - 189
  • 16
  • [ 100-97-0 ]
  • [ 90-05-1 ]
  • [ 2931-90-0 ]
  • [ 148-53-8 ]
  • [ 121-33-5 ]
YieldReaction ConditionsOperation in experiment
11.5%
Stage #1: With copper(I) oxide In trifluoroacetic acid for 5 h; Reflux
Stage #2: With hydrogenchloride In water at 20℃; for 1 h;
General procedure: To a solution of substrates (1a–1q, 0.15 mmol) in trifluoroacetic acid (5 ml), hexamethylenetetramine (0.3 mmol) and cuprous oxide (0.15 mmol) were added. The reaction mixture was refluxed for about 5 h, cooled to room temperature, followed by addition of hydrochloric acid (3 N, 5 ml). After stirring for another 1 h, the solution was concentrated under reduced pressure. The products were purified by silica gel column chromatography (200–300 mesh).
Reference: [1] Research on Chemical Intermediates, 2015, vol. 41, # 11, p. 8147 - 8158
  • 17
  • [ 24677-78-9 ]
  • [ 74-88-4 ]
  • [ 148-53-8 ]
  • [ 86-51-1 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1983, # 7, p. 400 - 401
  • 18
  • [ 2169-99-5 ]
  • [ 148-53-8 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 6, p. 1302 - 1304
  • 19
  • [ 50-00-0 ]
  • [ 90-05-1 ]
  • [ 148-53-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1939 - 1943
[2] Organic Letters, 2017, vol. 19, # 23, p. 6340 - 6343
[3] Organic Letters, 2018, vol. 20, # 10, p. 2880 - 2883
  • 20
  • [ 4383-05-5 ]
  • [ 148-53-8 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 7, p. 1542 - 1546
  • 21
  • [ 548756-56-5 ]
  • [ 1663-39-4 ]
  • [ 148-53-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 7, p. 1133 - 1138
  • 22
  • [ 67-66-3 ]
  • [ 90-05-1 ]
  • [ 148-53-8 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 2021
[2] Tetrahedron Asymmetry, 2008, vol. 19, # 15, p. 1813 - 1819
  • 23
  • [ 861779-85-3 ]
  • [ 148-53-8 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1926, vol. <2> 112, p. 63
  • 24
  • [ 90-05-1 ]
  • [ 76-03-9 ]
  • [ 148-53-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1927, vol. 46, p. 147
  • 25
  • [ 128404-89-7 ]
  • [ 79-04-9 ]
  • [ 87503-74-0 ]
  • [ 148-53-8 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 2, p. 535 - 539
  • 26
  • [ 15319-22-9 ]
  • [ 148-53-8 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1929, vol. 45, p. 528 - 534
[2] , Gmelin Handbook: Cu: MVol.B4, 162, page 1806 - 1809,
  • 27
  • [ 591-31-1 ]
  • [ 148-53-8 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1988, # 20, p. 1350 - 1352
  • 28
  • [ 877-22-5 ]
  • [ 148-53-8 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1926, vol. <2> 112, p. 63
  • 29
  • [ 861783-23-5 ]
  • [ 148-53-8 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1926, vol. <2> 112, p. 63
  • 30
  • [ 13664-27-2 ]
  • [ 148-53-8 ]
Reference: [1] , Gmelin Handbook: Cu: MVol.B4, 162, page 1806 - 1809,
  • 31
  • [ 90-05-1 ]
  • [ 864131-95-3 ]
  • [ 148-53-8 ]
Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 2406
  • 32
  • [ 67-66-3 ]
  • [ 90-05-1 ]
  • [ 621-59-0 ]
  • [ 148-53-8 ]
  • [ 121-33-5 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 8, p. 543 - 546
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 8, p. 543 - 546
  • 33
  • [ 54043-60-6 ]
  • [ 90-05-1 ]
  • [ 148-53-8 ]
  • [ 121-33-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 764
  • 34
  • [ 32752-36-6 ]
  • [ 90-05-1 ]
  • [ 148-53-8 ]
  • [ 121-33-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 764
  • 35
  • [ 90-05-1 ]
  • [ 91-78-1 ]
  • [ 148-53-8 ]
  • [ 121-33-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 764
  • 36
  • [ 91-10-1 ]
  • [ 934-00-9 ]
  • [ 24677-78-9 ]
  • [ 148-53-8 ]
  • [ 95-48-7 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 5, p. 1376 - 1389
  • 37
  • [ 225793-15-7 ]
  • [ 824-42-0 ]
  • [ 91-10-1 ]
  • [ 148-53-8 ]
  • [ 95-48-7 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 5, p. 1376 - 1389
  • 38
  • [ 148-53-8 ]
  • [ 17028-61-4 ]
YieldReaction ConditionsOperation in experiment
92% With yttrium(lll) nitrate hexahydrate In acetic acid at 20℃; for 0.166667 h; Phenol (94 mg, 1 mmol) dissolved in 3 mL glacial acetic acidin a 50 mL test tube was treated with solid Y(NO3)3.6H2O(383 mg, 1 mmol) with constant shaking at RT for 10 min.The reaction was monitored by TLC at 10percent EtOAc inPetroleum benzene. Ice-cold water (30 mL) was added to thereaction mixture after completion of reaction and left for 15min. Solid was collected by filtration and washed with water.Solid product isolated in this way was used for analysis withoutfurther purification. Experimental procedure for the synthesisof compounds 2a–2e is mentioned in the SupportingInformation.
Reference: [1] Journal of Chemical Sciences, 2017, vol. 129, # 1, p. 39 - 43
[2] Journal of Materials Chemistry C, 2018, vol. 6, # 43, p. 11536 - 11551
[3] Dyes and Pigments, 2017, vol. 136, p. 292 - 301
[4] Proceedings of the National Institute of Sciences of India, 1940, vol. 6, p. 641,656
[5] Justus Liebigs Annalen der Chemie, 1932, vol. 496, p. 125,140[6] Proceedings of the Imperial Academy (Tokyo), vol. 7, p. 256[7] Chem. Zentralbl., 1931, vol. 102, # II, p. 2623
[8] Archiv der Pharmazie (Weinheim, Germany), 1915, vol. 253, p. 40
[9] Magnetic Resonance in Chemistry, 1992, vol. 30, # 11, p. 1128 - 1131
[10] Synthetic Communications, 2007, vol. 37, # 20, p. 3599 - 3609
[11] Helvetica Chimica Acta, 1930, vol. 13, p. 482,486
[12] Tetrahedron, 2008, vol. 64, # 22, p. 5085 - 5090
  • 39
  • [ 148-53-8 ]
  • [ 4055-69-0 ]
Reference: [1] Journal of the Chemical Society, 1938, p. 1602,1605
[2] Journal fuer Praktische Chemie (Leipzig), 1938, vol. <2> 150, p. 257,260
  • 40
  • [ 148-53-8 ]
  • [ 24677-78-9 ]
YieldReaction ConditionsOperation in experiment
87% With aluminum (III) chloride; sodium iodide In acetonitrile at 80℃; for 18 h; Add acetonitrile (40ml) to a 100ml eggplant bottle,Aluminum trichloride (0.752g, 5.64mmol, 1.1eq),NaI (2.305 g, 15.38 mmol, 3.0 eq) and o-vanillin (0.780 g, 5.13 mmol),Heat to 80 ° C, stop stirring after 18 hours of reaction.After cooling to room temperature, it was acidified with 2 mol/L of dilute hydrochloric acid (10 ml), and extracted with ethyl acetate (50 ml × 3). The organic phase was combined and washed with saturated aqueous sodium thiosulfate (10 ml). Washed with saturated brine (10 ml), dried over anhydrous magnesium sulfate, filtered, evaporated, evaporated, evaporated. )purification,0.620 g of 2,3-dimethoxybenzaldehyde were obtained (yellow solid, yield 87percent).
86.5% With boron tribromide In dichloromethane at 20℃; for 15.5 h; Cooling with ice To a 500 ml three-necked flask was added 30.0 g of o-vanillin, 150 mL of dichloromethane, and placed in an ice bath.53.8 g of boron tribromide was dissolved in 20 mL of dichloromethane and added dropwise for 30 minutes. After the drop is finished, it rises to room temperature.Stirring was continued for 15 h. After adding 50 mL of water, stirring was continued for 1 hour, and the organic phase was separated and concentrated under reduced pressure.24.0 g of 2,3-dihydroxybenzaldehyde was obtained in a yield of 86.5percent and a content of 98.0percent.
85%
Stage #1: With sodium hydroxide In water for 0.5 h;
Stage #2: With dihydrogen peroxide In water at 60℃; for 24 h;
In 2L of four flasks add 121.0g (0.80 µM) (1.0eq) 3 - methoxy -2 - hydroxy benzaldehyde, then in 0.5h dropping in 25percent NaOH aqueous solution of 128g (0.80 µM) (1.0eq), then in 6h in extra drop of 10percent of the 940 ml (3.5eq) of H2O2, Dropped control temperature not exceeding 50 °C, after finishing dripping heating to 60 °C, thermal insulation reflux 18h. After the reaction by adding 10percent hydrochloric acid is acidified to pH=1 - 2, standing, dichloromethane is used for extraction, separating out the lower organic phase, desolution removing dichloromethane, distillation collection 115 - 120 °C/15mmHg fraction, after cooling to obtain the 84.2g yellow solid, namely 2, 3 - dihydroxy benzaldehyde, yield is 85percent, mp=104 - 105 °C.
77.7% With boron tribromide In dichloromethane at -78 - 20℃; for 1 h; Inert atmosphere 10 g (65.7 mmol) of o-vanillin was dissolved in 100 ml of anhydrous dichloromethane under a nitrogen atmosphere at minus 78 ° C.6.3 ml (65.7 mmol) of boron tribromide was added dropwise, and the reaction system was allowed to react at room temperature for one hour.After the reaction is completed, the solution is quenched by dropwise addition of a saturated ammonium chloride solution, and water is added to the reaction system.It was extracted three times with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate.Filter, concentrate, and separate the residue by column chromatography (ethyl acetate/petroleum ether=1:5),9.08 g of the title compound was obtained as a white solid with a yield of 77.7percent.
67% With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18 h; Add aluminum triiodide (2·240 g, 5 · 5 mmol), acetonitrile (40 ml) and DMSO (0.430 g, 5.5 mmol) to a 100 ml eggplant-shaped flask, and heat to 80 ° C with stirring, and stir for 0.5 hour. Then, o-vanillin (0.380 g, 2.5 mmol) was added, and the reaction was further stirred (80 ° C). After the reaction for 18 hours, the stirring was stopped. After cooling to room temperature, 2 mol/L of dilute hydrochloric acid (10 ml) was added to the eggplant-shaped flask. The mixture was extracted with EtOAc (EtOAc (EtOAc)EtOAc. Evaporate to dryness on a rotary evaporator, and the residue was purified by flash column chromatography (ethyl acetate / petroleum ether = 1:4, volume ratio) to give 0.232 g of 2,3-dihydroxybenzaldehyde (yellow solid, The rate is 67percent).
65% With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 8 h; General procedure: To a suspension of AlI3 (5.5 mmol, 1.1 equiv) in hot CH3CN (40 mL) were added sequentially DIC (0.379 g, 3 mmol, 0.6 equiv) and eugenol (1, 0.821 g, 5.0 mmol). The mixture was stirred for 18 h at 80 °C, and then it was cooled to r.t., acidified with HCl (2 mol/L, 10 mL), and extracted with EtOAc (3 × 50 mL). The organic phases were combined, washed with sat. aq Na2S2O3 (10 mL) and brine (10 mL), and was dried (MgSO4). The solvent was removed on a rotary evaporator and the residue was purified by flash column chromatography (PE/EtOAc, 4:1) to afford 2 (0.750 g, 99percent) as a white solid
65% With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 8 h; To a 100 ml eggplant flask were added aluminum triiodide (2.253 g), acetonitrile (40 ml) DIC (0.383 g) and o-vanillin (0. 763 g) were heated to 80 ° C and reacted for 8 hours to stop stirring, After cooling to room temperature, add 2 mol / L dilute hydrochloric acid (10 ml) to the eggplant flask, And extracted with ethyl acetate (50 ml X). The combined organic phases were washed first with a saturated aqueous solution of sodium thiosulfate (10 ml), washed with saturated brine (10 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated Instrument evaporated, The residue was purified by flash column chromatography (eluent: ethyl acetate / petroleum ether = 1: 3, volume ratio) To give 0.450 g of 2,3-dihydroxybenzaldehyde (yellow solid in 65percent yield)
37% With aluminium(III) iodide; calcium oxide In acetonitrile at 80℃; for 18 h; To a 100 ml eggplant flask was added aluminum triiodide (2.242 g, 5.5 mmol), acetonitrile (40 ml),CaO (0.420 g, 7.5 mmol) and o-vanillin (0.763 g, 5 mmol), heated to 80 °C,After 18 hours of reaction, stirring was stopped. After cooling to room temperature, 2 mol/L dilute hydrochloric acid (10 ml) was acidified in an eggplant-shaped flask.Extract with ethyl acetate (50ml x 3) and combine the organic phases and wash first with saturated aqueous sodium thiosulfate (10ml).It was washed with saturated brine (10 ml), dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to dryness on a rotary evaporator.The residue was purified by flash column chromatography (eluent: ethyl acetate/petroleum ether=1:3, volume ratio).0.259 g of 2,3-dihydroxybenzaldehyde was obtained (yellow solid, yield 37percent).

Reference: [1] Patent: CN108821955, 2018, A, . Location in patent: Paragraph 0021; 0022; 0025; 0026
[2] Patent: CN108178753, 2018, A, . Location in patent: Paragraph 0023-0025
[3] Journal of the American Chemical Society, 2007, vol. 129, # 45, p. 13808 - 13809
[4] Patent: CN106699722, 2017, A, . Location in patent: Paragraph 0050-0052
[5] Patent: CN107840845, 2018, A, . Location in patent: Paragraph 0179; 0180; 0181; 0182
[6] Patent: CN108821930, 2018, A, . Location in patent: Paragraph 0150-0152
[7] Synthesis (Germany), 2017, vol. 49, # 12, p. 2721 - 2726
[8] Patent: CN106866377, 2017, A, . Location in patent: Paragraph 0172; 0173
[9] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 3, p. 392 - 397
[10] Agricultural and Biological Chemistry, 1980, vol. 44, # 2, p. 235 - 243
[11] Tetrahedron, 1984, vol. 40, # 13, p. 2529 - 2535
[12] Patent: CN107473916, 2017, A, . Location in patent: Paragraph 0100-0102
[13] Chemische Berichte, 1910, vol. 43, p. 1813
[14] Justus Liebigs Annalen der Chemie, 1911, vol. 383, p. 315
[15] Biochemische Zeitschrift, 1920, vol. 108, p. 90[16] Angewandte Chemie, 1920, vol. 33, p. 137
  • 41
  • [ 91-10-1 ]
  • [ 934-00-9 ]
  • [ 24677-78-9 ]
  • [ 148-53-8 ]
  • [ 95-48-7 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 5, p. 1376 - 1389
  • 42
  • [ 10035-10-6 ]
  • [ 148-53-8 ]
  • [ 64-19-7 ]
  • [ 24677-78-9 ]
Reference: [1] Chemische Berichte, 1910, vol. 43, p. 1813
[2] Justus Liebigs Annalen der Chemie, 1911, vol. 383, p. 315
  • 43
  • [ 148-53-8 ]
  • [ 20035-41-0 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 27, p. 5129 - 5132
[2] Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4485 - 4489
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1090 - 1093
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3768 - 3771
[5] Patent: CN106905154, 2017, A,
[6] Patent: CN107266304, 2017, A,
[7] Patent: CN108358761, 2018, A,
[8] Patent: CN108358761, 2018, A,
[9] Patent: CN108484593, 2018, A,
  • 44
  • [ 148-53-8 ]
  • [ 877-22-5 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 22, p. 3835 - 3839
[2] Journal of Organic Chemistry, 1986, vol. 51, # 4, p. 567 - 569
[3] Archiv der Pharmazie (Weinheim, Germany), 1915, vol. 253, p. 40
[4] Journal of Organic Chemistry, 1947, vol. 12, p. 85,88
[5] Journal of the Chemical Society, 1923, vol. 123, p. 3174
[6] Archiv der Pharmazie (Weinheim, Germany), 1915, vol. 253, p. 40
  • 45
  • [ 148-53-8 ]
  • [ 5034-74-2 ]
YieldReaction ConditionsOperation in experiment
98% at 0 - 20℃; for 0.5 h; To a solution of o-vanillin (11; 4.0 g, 0.026 mol) in AcOH (80 mL) at 0°C was added NaOAc (2.37 g, 0.029 mol), followed by the dropwise additionof Br2 (1.49 mL, 0.029 mol). The solution was stirred at r.t. for30 min. H2O (100 mL) was added and the aqueous mixture extractedwith CH2Cl2 (3 × 80 mL). The combined organic extracts were washedwith H2O (100 mL) and brine (50 mL), dried (MgSO4) and the solventwas removed in vacuo. The crude product was purified by flash chromatography(19:1 hexanes–EtOAc) to yield the title compound 26(6.0 g, 98percent) as a yellow solid; mp 119–123 °C (Lit.19 mp 122–124 °C).1H NMR (400 MHz, CDCl3/TMS): δ = 3.92 (3 H, s, OCH3), 7.18 (1 H, d,J = 2.4 Hz, 4-H), 7.31 (1 H, d, J = 2.4 Hz, 6-H), 9.86 (1 H, s, CHO), 11.00(1 H, s, OH).13C NMR (100 MHz, CDCl3): δ = 56.3 (OCH3), 111.1 (C-5), 120.8 (C-6),121.3 (C-1), 126.1 (C-4), 149.3 (C-2), 150.9 (C-3), 195.4 (CHO).The 1H NMR and 13C NMR data were in agreement with literature values.19
82% With bromine In 1,2-dichloro-ethane at 20℃; for 1.5 h; To a well stirred mixture of o-vanillin (20 g, 130 mmol) in dichloroethane (75 mL), liquid bromine (23.2 g, 140 mmol) was added over a period of 0.5 h, at room temperature. The reaction was completed in 1 h (monitored by TLC). Ice cold water (50 mL) was added to the reaction mixture. The organic layer was separated and washed with water. It was dried over anhydrous Na2SO4. Dichloroethane was removed under reduced pressure to give a crude solid product. Which was recrystallized from dichloromethane : methanol (1:1) to give a pure 5-bromo-o-vanilin 5 (25 g, 82percent), mp 132-132 °C (lit. 127-129 °C).
81% With ammonium cerium (IV) nitrate; bromine; silica gel In tetrachloromethane at 20℃; for 24 h; Inert atmosphere To a suspension of o-vanillin 21 (1.0 g, 6.6 mmol) and silica (1.0 g) in wet CCl4 (10 mL), was added Br2 (0.34 mL, 6.6 mmol) and CAN (9 mg, 0.013 mmol) and the resultant mixture was stirred at room temperature for 24 h. The suspension was then diluted with CH2Cl2 (10 mL) and filtered through Celite. The filtrate was washed with a saturated aqueous solution of Na2S2O3 (50 mL), dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was purified by recrystallisation from 60percent ethanol/water to afford 5-bromo-2-hydroxy-3-methoxybenzaldehyde 22 (1.2 g, 81percent) as a yellow solid. RF (2:1 hexanes, ethyl acetate) 0.78; mp. 120.5-123.6 C (Lit: 122-123 C); dH (300 MHz; CDCl3; Me4Si) 3.91 (3H, s, OCH3), 7.15 (1H, s, 4-H), 7.28 (1H, s, 6-H), 9.84(1H, s, CHO), 10.99 (1H, s, OH); Spectroscopic data were in accordancewith literature values.
80% With bromine In acetic acid at 0℃; for 2 h; [0928] The solution of 2-hydroxy-3-methoxybenzaldeliyde (10.0 g, 65.79 mmole) in acetic acid (50 mL) was cooled to 0 °C (ice bath). Bromine (12.55 g, 78.95 mmole) was added dropwise to above solution, which was allowed to stir for 2 hours. The reaction was warmed to room temperature and diluted with water (100 mL). A light brown precipitate was formed. The solid was filtered and washed with water (50 mL). The filtrate was dried on high vacuum to give a light brown solid (12.2 g, 80.0percent) : GCMS M/Z 231. 0 (M+). HNMR (CDC13/400 MHz) 10.97 (s, 1H), 9.82 (s, 1H), 7.29 (s, 1H), 7.15 (s, 1H), 3.89 (m, 3H).

Reference: [1] Synthesis (Germany), 2017, vol. 49, # 6, p. 1190 - 1205
[2] Journal of the Iranian Chemical Society, 2011, vol. 8, # 2, p. 531 - 536
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, p. 503 - 508
[4] Chemische Berichte, 1986, vol. 119, # 4, p. 1374 - 1399
[5] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 6, p. 1119 - 1123
[6] Organic Process Research and Development, 2004, vol. 8, # 2, p. 201 - 212
[7] Organic and Biomolecular Chemistry, 2013, vol. 11, # 15, p. 2498 - 2513
[8] Tetrahedron, 1998, vol. 54, # 51, p. 15509 - 15524
[9] Synthetic Communications, 1991, vol. 21, # 8-9, p. 1091 - 1095
[10] Australian Journal of Chemistry, 1985, vol. 38, # 10, p. 1481 - 1489
[11] Tetrahedron, 2016, vol. 72, # 47, p. 7496 - 7504
[12] Tetrahedron, 2017, vol. 73, # 14, p. 1881 - 1894
[13] European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4689 - 4695
[14] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2001, vol. 56, # 6, p. 554 - 559
[15] Patent: WO2004/87686, 2004, A2, . Location in patent: Page 460
[16] Patent: WO2004/87687, 2004, A1, . Location in patent: Page 460
[17] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 23, p. 7164 - 7168
[18] Journal of Organic Chemistry, 2012, vol. 77, # 18, p. 8156 - 8166,11
[19] Journal of Organic Chemistry, 2012, vol. 77, # 18, p. 8156 - 8166
[20] Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 458 - 463[21] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 3, p. 522 - 528
[22] Chemistry - A European Journal, 2013, vol. 19, # 47, p. 15852 - 15855
[23] Journal of Medicinal Chemistry, 1995, vol. 38, # 12, p. 2251 - 2255
[24] Journal of Organic Chemistry, 1948, vol. 13, p. 489,493
[25] Archiv der Pharmazie (Weinheim, Germany), 1915, vol. 253, p. 40
[26] Journal of Organic Chemistry, 2014, vol. 79, # 9, p. 4104 - 4118
[27] RSC Advances, 2013, vol. 3, # 22, p. 8176 - 8179
[28] Organic Letters, 2016, vol. 18, # 8, p. 1752 - 1755
[29] Synlett, 2017, vol. 28, # 20, p. 2896 - 2900
[30] Organic and Biomolecular Chemistry, 2018, vol. 16, # 5, p. 832 - 837
  • 46
  • [ 1600-27-7 ]
  • [ 7732-18-5 ]
  • [ 148-53-8 ]
  • [ 64-19-7 ]
  • [ 5034-74-2 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 2279,2287
  • 47
  • [ 148-53-8 ]
  • [ 52924-54-6 ]
Reference: [1] Dyes and Pigments, 2017, vol. 136, p. 292 - 301
  • 48
  • [ 148-53-8 ]
  • [ 90-53-9 ]
Reference: [1] Yakugaku Zasshi, 1958, vol. 78, p. 798[2] Chem.Abstr., 1958, p. 18375
  • 49
  • [ 148-53-8 ]
  • [ 6342-70-7 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1915, vol. 253, p. 40
[2] Archiv der Pharmazie (Weinheim, Germany), 1915, vol. 253, p. 40
  • 50
  • [ 148-53-8 ]
  • [ 1312609-83-8 ]
Reference: [1] Patent: US2011/152246, 2011, A1,
  • 51
  • [ 148-53-8 ]
  • [ 1312610-07-3 ]
Reference: [1] Patent: US2011/152246, 2011, A1,
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 148-53-8 ]

Aryls

Chemical Structure| 2103-57-3

[ 2103-57-3 ]

2,3,4-Trimethoxybenzaldehyde

Similarity: 0.91

Chemical Structure| 4055-69-0

[ 4055-69-0 ]

2,3-Dihydroxy-4-methoxybenzaldehyde

Similarity: 0.91

Chemical Structure| 57415-35-7

[ 57415-35-7 ]

2-Methoxy-4-methylbenzaldehyde

Similarity: 0.91

Chemical Structure| 672-13-9

[ 672-13-9 ]

2-Hydroxy-5-methoxybenzaldehyde

Similarity: 0.91

Chemical Structure| 135-02-4

[ 135-02-4 ]

2-Methoxybenzaldehyde

Similarity: 0.89

Aldehydes

Chemical Structure| 2103-57-3

[ 2103-57-3 ]

2,3,4-Trimethoxybenzaldehyde

Similarity: 0.91

Chemical Structure| 4055-69-0

[ 4055-69-0 ]

2,3-Dihydroxy-4-methoxybenzaldehyde

Similarity: 0.91

Chemical Structure| 57415-35-7

[ 57415-35-7 ]

2-Methoxy-4-methylbenzaldehyde

Similarity: 0.91

Chemical Structure| 672-13-9

[ 672-13-9 ]

2-Hydroxy-5-methoxybenzaldehyde

Similarity: 0.91

Chemical Structure| 135-02-4

[ 135-02-4 ]

2-Methoxybenzaldehyde

Similarity: 0.89

Ethers

Chemical Structure| 2103-57-3

[ 2103-57-3 ]

2,3,4-Trimethoxybenzaldehyde

Similarity: 0.91

Chemical Structure| 4055-69-0

[ 4055-69-0 ]

2,3-Dihydroxy-4-methoxybenzaldehyde

Similarity: 0.91

Chemical Structure| 57415-35-7

[ 57415-35-7 ]

2-Methoxy-4-methylbenzaldehyde

Similarity: 0.91

Chemical Structure| 672-13-9

[ 672-13-9 ]

2-Hydroxy-5-methoxybenzaldehyde

Similarity: 0.91

Chemical Structure| 135-02-4

[ 135-02-4 ]

2-Methoxybenzaldehyde

Similarity: 0.89