[ CAS No. 619-12-5 ] {[proInfo.proName]}

Name: 619-12-5|4-Formyl-3-hydroxybenzoic acid|98%
Brand: Ambeed
SKU: A115469
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Quality Control of [ 619-12-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 619-12-5 ]

SDS Specification

Alternatived Products of [ 619-12-5 ]

Product Details of [ 619-12-5 ]

CAS No. :	619-12-5	MDL No. :	MFCD05865188
Formula :	C₈H₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FDDHFCWYCKQKGY-UHFFFAOYSA-N
M.W :	166.13	Pubchem ID :	317508
Synonyms :

Calculated chemistry of [ 619-12-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.81
TPSA :	74.6 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 :	No
Log Kp (skin permeation) :	-7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.62
Log Po/w (XLOGP3) :	0.42
Log Po/w (WLOGP) :	0.9
Log Po/w (MLOGP) :	0.38
Log Po/w (SILICOS-IT) :	0.89
Consensus Log Po/w :	0.64

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.37
Solubility :	7.04 mg/ml ; 0.0424 mol/l
Class :	Very soluble
Log S (Ali) :	-1.55
Solubility :	4.64 mg/ml ; 0.0279 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.14
Solubility :	12.1 mg/ml ; 0.0729 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.12

Safety of [ 619-12-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 619-12-5 ]

* 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 [ 619-12-5 ]
Downstream synthetic route of [ 619-12-5 ]

[ 619-12-5 ] Synthesis Path-Upstream 1~4

1
[ 67-56-1 ]
[ 619-12-5 ]
[ 24589-98-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 60℃; for 3 h;	Step 1: Synthesis of methyl 4-formyl-3-hydroxybenzoate (239) 4-Formyl-3-hydroxybenzoic acid (1.2 g, 7.22 mmol) was dissolved in MeOH (10 ml). SOCl2 (1.054 ml, 14.45 mmol) was added, and the reaction was stirred at 60° C. for 3 hours to achieve completion. The reaction mixture was concentrated, and the crude was triturated in Hexane and filtered to give methyl 4-formyl-3-hydroxybenzoate (1.3 g, 7.22 mmol, 100percent yield). MS/ESI⁺ 181.04 [MH]⁺
85%	Reflux	4-Formyl-3-hydroxybenzoic acid (5 g, 30 mmol) was suspended in methanol (70 mL), and treated with thionyl chloride (3.29 mL 45 mmol) dropwise. The mixture was heated to reflux overnight. Concentrated to dryness, and 50 mL of toluene was added, and concentrated again. The residue was recrystallized from ethyl acetate-hexane. A total of 4.8 g (85percent) of methyl 4-formyl-3-hydroxybenzoate was obtained.

Reference： [1] Patent: US2014/155391, 2014, A1, . Location in patent: Paragraph 0617; 0618
[2] Patent: US2012/245144, 2012, A1, . Location in patent: Page/Page column 105
[3] Journal of the American Chemical Society, 1955, vol. 77, p. 973,979
[4] Journal of Medicinal Chemistry, 1969, vol. 12, # 3, p. 420 - 424
[5] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 5, p. 1175 - 1183

2
[ 619-12-5 ]
[ 18107-18-1 ]
[ 24589-98-8 ]

Reference： [1] Patent: WO2006/90850, 2006, A1, . Location in patent: Page/Page column 65

3
[ 100-97-0 ]
[ 99-06-9 ]
[ 619-12-5 ]

Yield	Reaction Conditions	Operation in experiment
36%	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

4
[ 67-66-3 ]
[ 99-06-9 ]
[ 619-12-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1969, vol. 12, # 3, p. 420 - 424

[ 619-12-5 ] Synthesis Path-Downstream 1~88

1
[ 619-12-5 ]
(4-carboxy-2-hydroxy-phenyl)-acetic acid [ No CAS ]

Reference： [1]Acta Chemica Scandinavica (1947),1952,vol. 6,p. 433,438

2
[ 20439-47-8 ]
[ 619-12-5 ]
4-[(2-amino-cyclohexylimino)-methyl]-3-hydroxy-benzoic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 2591 - 2595

3
[ 619-12-5 ]
[ 18531-95-8 ]
C₃₆H₂₄N₂O₆ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 7712 - 7713

4
[ 619-12-5 ]
4-({2-[(3-<i>tert</i>-butyl-2-hydroxy-5-pyridin-4-yl-benzylidene)-amino]-cyclohexylimino}-methyl)-3-hydroxy-benzoic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 2591 - 2595

5
[ 619-12-5 ]
[ 330580-56-8 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 141 - 149

6
[ 619-12-5 ]
3-[benzoyl(methyl)amino]-3,4-dihydro-2-oxo-2H-1,3-benzoxazine-7-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 141 - 149

7
[ 619-12-5 ]
[ 330580-50-2 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 141 - 149

8
[ 619-12-5 ]
[ 330580-53-5 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 141 - 149

9
[ 619-12-5 ]
[ 330580-54-6 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 141 - 149

10
[ 619-12-5 ]
[ 330580-68-2 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 141 - 149

11
[ 619-12-5 ]
3-hydroxy-4-[(2-oxo-5-benzyl-3H-1,3,4-oxadiazol-3-yl)methyl]benzoic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 141 - 149

12
[ 619-12-5 ]
[ 330580-66-0 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 141 - 149

13
[ 619-12-5 ]
[ 330580-67-1 ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 141 - 149

14
[ 619-12-5 ]
(S)-4,5-Dihydro-2-(2-hydroxy-4-carboxyphenyl)-4-thiazolecarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 95 - 108

15
[ 619-12-5 ]
2-hydroxy-4-(α-hydroxy-benzhydryl)-benzophenone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 973,979

16
[ 619-12-5 ]
5-(α-Hydroxy-benzhydryl)-2-(α-hydroxy-benzyl)-phenol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 973,979

17
[ 619-12-5 ]
2-oxo-2,3-dihydro-benzofuran-6-carboxylic acid [ No CAS ]

Reference： [1]Acta Chemica Scandinavica (1947),1952,vol. 6,p. 433,438

18
[ 315-08-2 ]
[ 619-12-5 ]
[ 1073612-64-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 8187 - 8195

19
[ 619-12-5 ]
[ 36805-97-7 ]
[ 1017794-26-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	In tetrahydrofuran; for 1.5h;Reflux;	A solution of <strong>[619-12-5]4-formyl-3-hydroxybenzoic acid</strong> (1 g, 6.0 mmol) was dissolved in tetrahydrofuran (10 ml) and heated under reflux. Then N,N-dimethylformamide di-tert-butyl acetal was added dropwise (5.77 ml, 24.0 mmol) and the mixture was stirred at the temperature for 1.5 h. The cooled solution was concentrated under reduced pressure and the residue chromatographed on silica gel with cyclohexane/ethyl acetate as the eluent (gradient=1 hour from 0% ethyl acetate to 5% ethyl acetate).Yield: 1.13 g (84% of theory).HPLC-MS: logP=3.11; mass (m/z): 223.1 (M+H)+; 1H NMR (CD3CN) 1.58 (s, 9H), 7.48 (s, 1H), 7.57 (d, 1H), 7.76 (d, 1H).
6.95 g	In tetrahydrofuran; for 1.5h;Reflux;	A solution of <strong>[619-12-5]4-formyl-3-hydroxybenzoic acid</strong> (6.19 g, 37.3 mmol) in 56 mL of anhydrous THF washeated to reflux, 1,1-di-tert-butoxy-N,N-dimethylmethanamine (35.7 mL, 149 mmol) was addeddropwise and the mixture was stirred at reflux for 1.5 hr. After cooled the reaction to RT, the reaction solution was concentrated in vacuo. The residue was purified by silica gel flash chromatography (100% heptane - 5% ethyl acetate/heptane) to give tert-butyl 4-formyl-3- hydroxybenzoate (6.95 g). LCMS retention time = 1.39 minutes (LC method 3); MS (m+1) = 223.1.1H NMR (400 MHz, DMSO-d5) 51.54 (s, 9H), 7.41 (ddd, J= 8.1, 1.4, 0.6 Hz, IH), 7.54 (d, J= 1.4 Hz, IH), 7.72 (d, J= 8.1 Hz, IH), 10.31 -10.37 (m, IH), 11.00 (s, IH).

Reference： [1]Patent: US2011/105532,2011,A1 .Location in patent: Page/Page column 44
[2]Patent: WO2019/87162,2019,A1 .Location in patent: Page/Page column 29

20
[ 619-12-5 ]
[ 1299483-17-2 ]

Reference： [1]Patent: US2011/105532,2011,A1
[2]Patent: WO2019/87162,2019,A1

21
[ 619-12-5 ]
[ 1299483-18-3 ]

Reference： [1]Patent: US2011/105532,2011,A1

22
[ 619-12-5 ]
[ 1299483-19-4 ]

Reference： [1]Patent: US2011/105532,2011,A1

23
[ 619-12-5 ]
[ 1299483-20-7 ]

Reference： [1]Patent: US2011/105532,2011,A1
[2]Patent: US2011/105532,2011,A1

24
[ 619-12-5 ]
[ 1299482-57-7 ]

Reference： [1]Patent: US2011/105532,2011,A1
[2]Patent: US2011/105532,2011,A1

25
[ 455-14-1 ]
[ 619-12-5 ]
C₁₅H₁₂F₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 2h;	To a mixture of <strong>[619-12-5]4-formyl-3-hydroxy-benzoic acid</strong> (206 mg, 1.20 mmol), 4-(trifluoromethyl)aniline (124 uL, 1.00 mmol), acetic acid (114 uL, 2.0 mmol) in 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (318 mg, 1.50 mmol). The reaction mixture was stirred at room temperature for 2 hr. To the above mixture was added isovaleraldehyde (1.30 uL, 1.20 mmol), sodium triacetoxyborohydride (318 mg, 1.50 mmol), and acetic acid (114 uL, 2.0 mmol). The reaction mixture was stirred at room temperature overnight. Added more Isovaleraldehyde (65 uL, 0.60 mmol), sodium triacetoxyborohydride (160 mg, 0.75 mmol) and 1,2-dichloroethane (1 mL)., and stirred at room temperature overnight. LC-MS shows mainly desired product, plus trace of intermediate. The reaction mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to get 440 mg crude acid as a yellow oil.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7277 - 7280

26
[ 619-12-5 ]
C₂₈H₂₇F₆NO₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7277 - 7280

27
[ 619-12-5 ]
C₃₀H₃₁F₆NO₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7277 - 7280

28
[ 619-12-5 ]
[ 1352573-58-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7277 - 7280

29
[ 619-12-5 ]
C₂₇H₂₄ClF₆NO [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7277 - 7280

30
[ 619-12-5 ]
C₂₈H₂₅F₆N₃O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7277 - 7280

31
[ 619-12-5 ]
[ 1257394-31-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7277 - 7280

32
[ 619-12-5 ]
C₂₀H₂₂F₃NO₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7277 - 7280

33
[ 619-12-5 ]
[ 1352573-59-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7277 - 7280

34
[ 619-12-5 ]
[ 1352573-60-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7277 - 7280

35
[ 619-12-5 ]
[ 1402345-15-6 ]

Reference： [1]Patent: US2012/258982,2012,A1

36
[ 619-12-5 ]
[ 1402345-16-7 ]

Reference： [1]Patent: US2012/258982,2012,A1

37
[ 619-12-5 ]
[ 1402345-17-8 ]

Reference： [1]Patent: US2012/258982,2012,A1

38
[ 619-12-5 ]
[ 1402345-18-9 ]

Reference： [1]Patent: US2012/258982,2012,A1

39
[ 619-12-5 ]
[ 1402345-19-0 ]

Reference： [1]Patent: US2012/258982,2012,A1

40
[ 619-12-5 ]
[ 1282516-27-1 ]

Reference： [1]Patent: US2012/245144,2012,A1

41
[ 619-12-5 ]
[ 1282516-29-3 ]

Reference： [1]Patent: US2012/245144,2012,A1

42
[ 619-12-5 ]
[ 1282516-62-4 ]

Reference： [1]Patent: US2012/245144,2012,A1

43
[ 619-12-5 ]
[ 1282516-54-4 ]

Reference： [1]Patent: US2012/245144,2012,A1

44
[ 619-12-5 ]
[ 1282516-55-5 ]

Reference： [1]Patent: US2012/245144,2012,A1

45
[ 619-12-5 ]
[ 1282516-61-3 ]

Reference： [1]Patent: US2012/245144,2012,A1

46
[ 619-12-5 ]
[ 1282516-63-5 ]

Reference： [1]Patent: US2012/245144,2012,A1

47
[ 619-12-5 ]
[ 1282516-64-6 ]

Reference： [1]Patent: US2012/245144,2012,A1

48
[ 619-12-5 ]
C₂₅H₁₉N₂O₆^(1-)*K⁽¹⁺⁾ [ No CAS ]

Reference： [1]Patent: US2012/258982,2012,A1

49
[ 619-12-5 ]
3-[4-((1S,2S,3R,5S,7S)-5-hydroxy-adamantan-2-ylcarbamoyl)-2-methoxy-benzyl]-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Patent: US2012/258982,2012,A1

50
[ 109-01-3 ]
[ 619-12-5 ]
[ 1446332-91-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃; for 3h;	Step A: 4-Formyl-3-hydroxybenzoic acid (830 mg, 5 mmol) was combined with 1- methylpiperazine (0.61 mL, 5.5 mmol), triethylamine (0.77 mL, 5.5 mmol) and (benzotriazol-1- yloxy)tripyrrolidinophosphonium hexafluorophosphate (2.86 g, 5.5 mmol) in CH2CI2 (10 mL). The mixture was stirred at room temperature for 3h, then concentrated and purified by silica gel column chromatography (0-5% MeOH in CH2CI2) to afford 2-hydroxy-4-(4-methylpiperazine-l- carbonyl)benzaldehyde (1.24 g, 100%). MS m/z 249.1 [M+H]+.
100%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃; for 3h;	Step A: 4-Formyl-3-hydroxybenzoic acid (830 mg, 5 mmol) was combined with 1-methylpiperazine (0.61 mL, 5.5 mmol), triethylamine (0.77 mL, 5.5 mmol) and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (2.86 g, 5.5 mmol) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 3 h, then concentrated and purified by silica gel column chromatography (0-5% MeOH in CH2Cl2) to afford 2-hydroxy-4-(4-methylpiperazine-1-carbonyl)benzaldehyde (1.24 g, 100%). MS m/z 249.1 [M+H]+.

Reference： [1]Patent: WO2013/101974,2013,A1 .Location in patent: Paragraph 00652; 00653
[2]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 335

51
[ 619-12-5 ]
[ 75-03-6 ]
ethyl 3-ethoxy-4-formylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 72h;	To a solution of <strong>[619-12-5]4-formyl-3-hydroxybenzoic acid</strong> (1.0 g, 6.02 mmol) in DMF (20 mE) was added potassium carbonate (2.49 g, 18.1 mmol) and ethyl iodide (2.82 g, 18.1 mmol). The reaction mixture was stirred at room temperature for 72 hours. The reaction mixture was concentrated at reduced pressure and the residue partitioned between ethyl acetate and watet The organic extract was washed with brine (x2), poured through a hydrophobic fit and the solvent evaporated at reduced pressure. The residue was purified by flash colunm chromatography (eluent-100% i-hexane to 4:1 i-hexane/ethyl acetate) to afford the title compound (1.41 g, 100%). 1H NMR (400 MHz, CDC13); oe 10.55 (s, 1H), 7.87 (d, J=8.3 Hz, 1H), 7.66 (d, J=8.3 Hz, 2H), 4.40 (q, J=7.2 Hz, 2H), 4.23 (q, J=7.0 Hz, 2H), 1.51 (dd, J=6.9, 6.9 Hz, 3H), 1.41 (dd, J=7.1, 7.1 Hz, 3H).
100%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 72h;	Synthesis of ethyl 3-ethoxy-4-formylbenzoate A solution of <strong>[619-12-5]4-formyl-3-hydroxybenzoic acid</strong> (1.0 g, 6.02 mmol) in DMF (20 mL) was added with potassium carbonate (2.49 g, 18.1 mmol) and ethyl iodide (2.82 g, 18.1 mmol). The reaction mixture was stirred at room temperature for 72 hours. The reaction mixture was concentrated at reduced pressure and the residue partitioned between ethyl acetate and water. The organic extract was washed with brine (*2), poured through a hydrophobic frit and the solvent evaporated at reduced pressure. The residue was purified by flash column chromatography (eluent-100% i-hexane to 4:1 i-hexane/ethyl acetate) to afford the title compound (1.41 g, 100%). 1H NMR (400 MHz, CDCl3); delta 10.55 (s, 1H), 7.87 (d, J=8.3 Hz, 1H), 7.66 (d, J=8.3 Hz, 2H), 4.40 (q, J=7.2 Hz, 2H), 4.23 (q, J=7.0 Hz, 2H), 1.51 (dd, J=6.9, 6.9 Hz, 3H), 1.41 (dd, J=7.1, 7.1 Hz, 3H).
18%	With caesium carbonate; In acetonitrile; for 4h;Reflux;	To a solution of <strong>[619-12-5]4-formyl-3-hydroxybenzoic acid</strong> (3.01 mmol, 500 mg) in ACN (3ml), iodoethane (9.03 mmol, 1408 mg) and cesium carbonate (9.03 mmol, 2942 mg) were added. The reaction mixture was refluxed for 4h. Solvents were evaporated. It was washed twice with EtAcO / water. The combined organic layers were dried over anhydrous Na2S04, filtered and evaporated (121 mg, yield: 18%). LC-MS: tR = 2.33 [M+H]+ = 223 (method 6)

Reference： [1]Patent: US2016/235734,2016,A1 .Location in patent: Paragraph 0512; 0513
[2]Patent: US2018/16267,2018,A1 .Location in patent: Paragraph 0226; 0227
[3]Patent: WO2013/149997,2013,A1 .Location in patent: Page/Page column 147

52
[ 619-12-5 ]
[ 75-03-6 ]
[ 126200-19-9 ]

Yield	Reaction Conditions	Operation in experiment
39%	With cesium fluoride; In N,N-dimethyl-formamide; at 20℃; for 144h;	Ethyl 4-formyl-3 -hydroxybenzoate (161 6-44a). To a solution of 4-formyl-3 - hydroxybenzoic acid (0.43 g, 2.6 mmol) in DMF (0.52 mL, 5.0 M) was added cesium fluoride (0.59 g, 3.9 mmol) and iodoethane (0.23 mL, 2.9 mmol, 1.1 equiv). The reaction mixture stirred at rt for 6 days before being concentrated in vacuo, diluted with water andextracted with DCM (2x). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Purification was achieved via flash column chromatography on Si02 (Hexanes/EtOAc: 1/1) to afford a white solid (0.19 g, 39 %).

Reference： [1]Patent: WO2014/25942,2014,A1 .Location in patent: Page/Page column 54
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2334 - 2356

53
[ 619-12-5 ]
[ 1560893-00-6 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2334 - 2356

54
[ 619-12-5 ]
[ 1560894-91-8 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2334 - 2356

55
[ 619-12-5 ]
[ 1548871-69-7 ]