[ CAS No. 118-55-8 ] {[proInfo.proName]}

Name: 118-55-8|Phenyl Salicylate|98%
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Quality Control of [ 118-55-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 118-55-8 ]

Product Details of [ 118-55-8 ]

CAS No. :	118-55-8	MDL No. :	MFCD00002213
Formula :	C₁₃H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZQBAKBUEJOMQEX-UHFFFAOYSA-N
M.W :	214.22	Pubchem ID :	8361
Synonyms :

Calculated chemistry of [ 118-55-8 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	59.87
TPSA :	46.53 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 :	No
Log Kp (skin permeation) :	-4.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.98
Log Po/w (XLOGP3) :	3.83
Log Po/w (WLOGP) :	2.61
Log Po/w (MLOGP) :	2.81
Log Po/w (SILICOS-IT) :	2.43
Consensus Log Po/w :	2.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.94
Solubility :	0.0247 mg/ml ; 0.000115 mol/l
Class :	Soluble
Log S (Ali) :	-4.5
Solubility :	0.00673 mg/ml ; 0.0000314 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.04
Solubility :	0.0198 mg/ml ; 0.0000923 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.73

Safety of [ 118-55-8 ]

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 [ 118-55-8 ]

* 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 [ 118-55-8 ]
Downstream synthetic route of [ 118-55-8 ]

[ 118-55-8 ] Synthesis Path-Upstream 1~8

1
[ 118-55-8 ]
[ 97-05-2 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1900, vol. <2> 61, p. 545

2
[ 118-55-8 ]
[ 89-73-6 ]

Reference： [1] Oriental Journal of Chemistry, 2012, vol. 28, # 4, p. 1841 - 1844

3
[ 118-55-8 ]
[ 89-73-6 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 199 - 208

4
[ 118-55-8 ]
[ 109-89-7 ]
[ 19311-91-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 199 - 208
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 2913

5
[ 123-30-8 ]
[ 118-55-8 ]
[ 526-18-1 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1900, vol. <2> 61, p. 552[2] Chem. Zentralbl., 1900, vol. 71, # II, p. 612
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 2913
[4] Org.Synth.Coll.Vol.III <1955> 765,
[5] J.Textile Inst., 1930, vol. 21, p. 245T,255T
[6] Journal fuer Praktische Chemie (Leipzig), 1900, vol. <2> 61, p. 552[7] Chem. Zentralbl., 1900, vol. 71, # II, p. 612
[8] Journal of the American Chemical Society, 1947, vol. 69, p. 2913
[9] Org.Synth.Coll.Vol.III <1955> 765,

6
[ 118-55-8 ]
[ 6329-74-4 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1895, vol. <2> 51, p. 212

7
[ 118-55-8 ]
[ 54-21-7 ]

Reference： [1] Journal of Molecular Catalysis A: Chemical, 2014, vol. 396, p. 23 - 30

8
[ 118-55-8 ]
[ 875664-25-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 44, p. 13809 - 13813[2] Angew. Chem., 2017, vol. 129, # 44, p. 13997 - 14001,5

[ 118-55-8 ] Synthesis Path-Downstream 1~88

1
[ 186581-53-3 ]
[ 118-55-8 ]
[ 10268-71-0 ]

Reference： [1]Chemische Berichte,1906,vol. 39,p. 1558
[2]Chemische Berichte,1906,vol. 39,p. 1558

2
[ 504-29-0 ]
[ 118-55-8 ]
[ 13563-04-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	at 190 - 210℃; for 1.5h;
50%	210 deg C, 1.5 h; ethanol, reflux, 5 min.;
	With 1,2,4-Trichlorobenzene

	at 210℃; for 1.5h;
	With sodium hydroxide In water; acetonitrile at 30℃; pH=11.51-12.29;

Reference： [1]Waisser, Karel; Drazkova, Katerina; Kunes, Jiri; Klimesova, Vera; Kaustova, Jarmila [Il Farmaco, 2004, vol. 59, # 8, p. 615 - 625]
[2]Daidone; Raffa; Plescia; Matera; Caruso; Leone; Amico-Roxas [Il Farmaco, 1989, vol. 44, # 5, p. 465 - 473]
[3]Allen; van Allan [Organic Syntheses, 1955, vol. Coll. Vol. III, p. 765]
[4]Daidone; Maggio; Schillaci [Pharmazie, 1990, vol. 45, # 6, p. 441 - 442]
[5]Khan, Mohammad Niyaz [Journal of the Chemical Society. Perkin transactions II, 1989, p. 199 - 208]

3
[ 3325-11-9 ]
[ 118-55-8 ]
N-(1H-benzotriazol-5-yl)-salicylamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 2913

4
[ 123-30-8 ]
[ 118-55-8 ]
[ 526-18-1 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1900,vol. <2> 61,p. 552
Chemisches Zentralblatt,1900,vol. 71,p. 612
[2]Journal of the American Chemical Society,1947,vol. 69,p. 2913
[3],1930,vol. 21,p. 245T,255T
[4]Journal fur praktische Chemie (Leipzig 1954),1900,vol. <2> 61,p. 552
Chemisches Zentralblatt,1900,vol. 71,p. 612
[5]Journal of the American Chemical Society,1947,vol. 69,p. 2913

5
[ 3365-85-3 ]
[ 118-55-8 ]
[ 117042-61-2 ]

Reference： [1]Journal of Organic Chemistry,1956,vol. 21,p. 1152,1154

6
[ 103-90-2 ]
[ 118-55-8 ]
[ 118-57-0 ]

Yield	Reaction Conditions	Operation in experiment
	at 200 - 210℃;
	at 210 - 225℃;

Reference： [1]Cohn,G. [Journal fur praktische Chemie (Leipzig 1954), 1900, vol. <2> 61, p. 552][Chemisches Zentralblatt, 1900, vol. 71, # II, p. 612]
[2]Schwyzer,J. [Die Fabrikation pharmazeutischer und chemisch-technischer Produkte <Berlin 1931>,S.259]

7
[ 118-55-8 ]
[ 106-49-0 ]
[ 7164-80-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With boron trifluoride diethyl etherate; In toluene; at 20℃;	Step al) 2-Hvdroxy-N-p-tolyl -benzamide One drop of boron trifluoride diethyl etherate was added to a solution of 2-hydroxybenzoic acid phenyl ester (1 g, 46.7 mmol) and 4-toluidine (0.5 g, 46.7 mmol) in toluene (5 mL). The reaction mixture obtained was kept at RT overnight. A crystalline precipitate formed, the crystals were collected by filtration, washed 3 times with cold MTBE and dried in vacuo to afford 2-hydroxy-N-p-tolyl-benzamide in the form of colorless crystals (0.81 g, 76% of theory). Chemical characterization data correspond to data derived from the known compound (CAS 7164-80-9).

Reference： [1]Monatshefte fur Chemie,2003,vol. 134,p. 1215 - 1219
[2]Patent: WO2013/186153,2013,A2 .Location in patent: Page/Page column 45
[3]Bulletin de la Societe Chimique de France,1958,p. 185

8
[ 118-55-8 ]
[ 108-45-2 ]
[ 25591-53-1 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 2913
[2]Journal of the American Chemical Society,1947,vol. 69,p. 2913
[3],1930,vol. 21,p. 245,255

9
[ 118-55-8 ]
[ 107-15-3 ]
[ 6345-72-8 ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 2512 - 2521
[2]Il Farmaco,1990,vol. 45,p. 285 - 292
[3]European Journal of Inorganic Chemistry,2020,vol. 2020,p. 382 - 393
[4]Journal of the American Chemical Society,1947,vol. 69,p. 2913

10
[ 118-55-8 ]
[ 109-89-7 ]
[ 19311-91-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1989,p. 199 - 208
[2]Journal of the American Chemical Society,1947,vol. 69,p. 2913

11
[ 118-55-8 ]
[ 77-78-1 ]
[ 10268-71-0 ]

Reference： [1]Industrial and Engineering Chemistry,1951,vol. 43,p. 1585,1588

12
[ 118-55-8 ]
[ 74-89-5 ]
[ 1862-88-0 ]

Reference： [1]Journal of the Chemical Society,1907,vol. 91,p. 194
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1994,vol. 33,p. 752 - 757
[3]Journal of the Chemical Society,1907,vol. 91,p. 194

13
[ 118-55-8 ]
[ 135-19-3 ]
[ 613-78-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 180 - 200℃;

Reference： [1]Cohn,G. [Journal fur praktische Chemie (Leipzig 1954), 1900, vol. <2> 61, p. 552][Chemisches Zentralblatt, 1900, vol. 71, # II, p. 612]
[2]Cohn,G. [Journal fur praktische Chemie (Leipzig 1954), 1900, vol. <2> 61, p. 552][Chemisches Zentralblatt, 1900, vol. 71, # II, p. 612]
[3]Current Patent Assignee: Cohn,G. - DE111656, 1800, C

14
[ 69-72-7 ]
[ 108-95-2 ]
[ 118-55-8 ]

Yield	Reaction Conditions	Operation in experiment
		Salicylic acid-based compound (15,1eq.) Added to the reaction solvent methylene chloride, SOCl2 (3eq.) Was added dropwise to the solution. The resulting reaction mixture was reacted at 50 1h after the spin evaporated on a rotary evaporator to remove SOCl2. The resulting crude product was dissolved using methylene chloride, then added dropwise phenol (phenol, 1eq.) And triethylamine (TEA, 3eq.) In a mixture of dichloromethane. The resulting reaction mixture was stirred at r.t. 1h, quenched with water. Extracted with dichloromethane, the organic phases were dried over anhydrous magnesium sulfate. After the desiccant was filtered, the organic phase was mixed with silica gel column chromatography using silica gel, yielding intermediate 16. Intermediate 16 (1eq.) And 1,1,3,3-tetramethylguanidine (TMG, 1.5eq.) Was added the reaction solvent, N, N- dimethylformamide, and stirred 5min, guanidine compound ( 17,1.6eq.), stirred at room temperature overnight. Completion of the reaction was quenched with water, extracted with ethyl acetate after using silica gel column chromatography to obtain benzoyl guanidine compound (18). Intermediate 16, O- benzotriazole (1eq.) - (. HBTU, 1.6eq) tetramethyluronium hexafluorophosphate, N, N- diisopropylethylamine (. DIEA, 3eq) was added Solvent N, N- dimethyl formamide. The reaction was stirred at rt for 30min, amidino compound (19,1.2eq.) Added to the reaction mixture. The reaction mixture was stirred at room temperature overnight, quenched with water. After extraction with ethyl acetate, silica gel column chromatography to obtain the amidine-benzoyl compound (20).
85.11%Chromat.	With sulfonated silica; under 760.051 Torr; for 0.15h;Microwave irradiation;	General procedure: In all reactions involving SiO2-SO3H, the amounts of carboxylicacid (1.0 mmol) and phenol (0.0941 g, 1.00 mmol) were uniform. The amount of catalyst in each run wasadjusted to maintain a constant (10%) mass-to-mass ratioto the phenol. All reactions were heated with a heatingmantle (5 h, the final temperature of the slurries did notexceed 120 C) or by irradiation (5 or 9 min) in an unmodifiedMW oven (900 GHz)/360 W using an unstoppered125-mL two-necked round bottom flask.2 The final temperatureof the slurries did not exceed 73 C.

Reference： [1]Synthetic Communications,2006,vol. 36,p. 2975 - 2981
[2]Chemical Papers,2011,vol. 65,p. 52 - 59
[3]Journal fur praktische Chemie (Leipzig 1954),1885,vol. <2> 31,p. 470
[4]Journal fur praktische Chemie (Leipzig 1954),1885,vol. <2> 31,p. 470
[5]Journal fur praktische Chemie (Leipzig 1954),1885,vol. <2> 31,p. 470
[6]Journal fur praktische Chemie (Leipzig 1954),1885,vol. <2> 31,p. 470
[7]Patent: US1995402,1932,
[8]Journal of the American Chemical Society,1953,vol. 75,p. 5417
[9],1927,vol. 68,p. 795
 Chemisches Zentralblatt,1928,vol. 99,p. 903
[10],1927,vol. 68,p. 795
 Chemisches Zentralblatt,1928,vol. 99,p. 903
[11]Gazzetta Chimica Italiana,1900,vol. 30 II,p. 348
 Gazzetta Chimica Italiana,1901,vol. 31 II,p. 83
[12]LA [reports]. U.S. Atomic Energy Commission,1945,vol. XXIII 12,p. 1,65
[13]Organic and Biomolecular Chemistry,2010,vol. 8,p. 2961 - 2967
[14]Patent: CN105523955,2016,A .Location in patent: Paragraph 0164; 0165; 0291
[15]Patent: DE565969,1940,
 DRP/DRBP Org.Chem.,
[16]Patent: DE43713,
[17]Patent: DE43713,
[18]Patent: DE43713,
[19]Patent: DE38973,
 Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 1,p. 237,2 134
[20]Patent: DE38973,
 Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 1,p. 237,2 134
[21]Journal of Nanoscience and Nanotechnology,2019,vol. 19,p. 3663 - 3668

15
[ 108-95-2 ]
[ 119-36-8 ]
[ 118-55-8 ]

Yield	Reaction Conditions	Operation in experiment
	Reflux;	General procedure: Typically, a liquid phase transesterification of methyl salicylate (MS) with phenol (P) was carried out by taking MS: P in 2: 1 ratio. The reactants along with the catalytic material (either honeycomb coated or powder forms of ZrO2, Mo/ZrO2 and W/ZrO2) were placed in the reactor and refluxed for a definite period of time. The total volume of the reaction mixture was always kept constant at 20 mL. After a definite period of time, the reaction mixture was cooled to room temperature, the catalytic material was separated from the reaction mixture, and the products obtained by the transesterification reaction were analyzed quantitatively by gas chromatograph (Mayura) fitted with a (10% SE-30 chromosorb w-AW, 3 m × 1/8?) column coupled with FID detector and qualitatively by GC-MS (Varian).Similarly, transesterification reactions of methyl salicylate with benzyl alcohol or cyclohexanol were carried out under a definite set of reaction conditions over both honeycomb coated and powder forms of ZrO2, Mo/ZrO2 and W/ZrO2.

Reference： [1]Journal of the Korean Chemical Society,2012,vol. 56,p. 563 - 570
[2]Patent: US2141985,1937,
[3]Journal of Chemical Sciences,2010,vol. 122,p. 193 - 201
[4]Comptes Rendus Chimie,2012,vol. 15,p. 799 - 807

16
[ 45865-42-7 ]
[ 118-55-8 ]
[ 22274-90-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1969,vol. 5,p. 46 - 48
Khimiya Geterotsiklicheskikh Soedinenii,1969,vol. 5,p. 56 - 58

17
[ 29927-08-0 ]
[ 118-55-8 ]
[ 123199-79-1 ]

Reference： [1]Il Farmaco,1989,vol. 44,p. 465 - 473
[2]Pharmazie,1990,vol. 45,p. 441 - 442

18
[ 118-55-8 ]
[ 109-76-2 ]
[ 24350-72-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	In isopropyl alcohol; at 20℃;	General procedure: A solution of phenyl salicylate (2.13 g, 9.9 mmol) in 2-propanol (30 mL) was added to a 2-propanol solution (10 mL) containing 1,2-diamino-2-methylpropane (0.93 g, 10.6 mmol) dropwise with stirring. The mixture was stirred overnight at room temperature. The resulting white precipitate was collected by filtration, washed with 2-propanol and diethyl ether, and dried in vacuo.

Reference： [1]Chemistry Letters,2011,vol. 40,p. 696 - 698
[2]Inorganica Chimica Acta,2013,vol. 399,p. 131 - 137
[3]Journal of the Chemical Society. Perkin transactions II,1989,p. 199 - 208
[4]Dalton Transactions,2018,vol. 47,p. 9575 - 9578

19
[ 118-55-8 ]
[ 135-19-3 ]
[ 1931-53-9 ]
[ 613-78-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 56% 2: 29%	at 260 - 285℃;
1: 56% 2: 29%	at 260 - 285℃; other temperature; other phenols;

Reference： [1]Kamat, S. P.; Paknikar, S. K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 38 - 41]
[2]Kamat, S. P.; Paknikar, S. K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 38 - 41]

20
[ 118-55-8 ]
[ 89-73-6 ]
O-salicylylhydroxylamine [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1989,p. 199 - 208

21
[ 118-55-8 ]
[ 69-72-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; cetyltrimethylammonim bromide; sodium hydroxide; In water; at 31.84℃;Micellar solution;Kinetics; Mechanism;	The kinetics of the hydrolytic cleavage of phenyl salicylateunder weakly alkaline medium (0.005-0.1 mol L-1NaOH) in 4%aqueous ethanol solvent in the presence and in the absence of sur-factants were studied spectrophotometrically by using UV-visibleShimadzu 1800 spectrophotometer with thermostatted cell com-partments and quartz cells with 1.0 cm path lengths. Appropriatequantities of solutions of PhS, aqueous ethanol and Milliporewater were placed in the cuvette. After ensuring thorough mix-ing and temperature equilibration, the reaction was initiated byadding requisite amount of NaOH solution. The time-resolvedspectra (scanning time interval: 150 s) of the reaction mixture([PhS] = 2.0 × 10-4mol L-1, [OH-] = 0.01 mol L-1, 4% (v/v) aqueousethanol) show maximum absorbance at 340 nm (Fig. 1). There isno apparent shift of the absorption peak near max, indicating thatthe concentration of any reaction intermediate during the reactioncourse would be very low. The absorbance at the maxdecreasesgradually with time indicating the progress of the reaction.Thus, the kinetics of the reaction was followed by monitor-ing the absorbance of the reaction mixture at 340 nm [33]. Thereaction was studied under pseudo-first order conditions, where[OH-] [PhS]. Under such conditions, the observed pseudo-firstorder rate constant (kobs) was calculated from Eq. (1) using thenon-linear least-square technique.

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 9768 - 9779
[2]Tetrahedron Letters,1988,vol. 29,p. 6893 - 6896
[3]Journal of the Chemical Society. Perkin transactions II,1986,p. 655 - 660
[4]Journal of Physical Organic Chemistry,2001,vol. 14,p. 669 - 676
[5]Journal of Molecular Catalysis A: Chemical,2015,vol. 396,p. 23 - 30

22
[ 118-55-8 ]
[ 57999-06-1 ]
N-(4-fenilpirazol-5-il)salicilammide [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1985,vol. 40,p. 683 - 694

23
[ 118-55-8 ]
[ 23286-70-6 ]
N-saliciloil-3-metil-4-carboetossi-5-amminopirazolo [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	at 210 - 215℃; for 1.5h;

Reference： [1]Daidone; Plescia; Raffa; Bajardi; Milici [Farmaco, Edizione Scientifica, 1985, vol. 40, # 9, p. 683 - 694]

24
[ 118-55-8 ]
[ 87-60-5 ]
N-(3-chloro-2-methyl-phenyl)-2-hydroxy-benzamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2004,vol. 39,p. 11 - 26

25
[ 118-55-8 ]
[ 88284-48-4 ]
[ 90-47-1 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 4273 - 4275

26
[ 124-38-9 ]
[ 100-67-4 ]
[ 102-09-0 ]
[ 118-55-8 ]

Reference： [1]Chemistry Letters,2006,vol. 35,p. 784 - 785

27
[ 124-38-9 ]
[ 108-95-2 ]
[ 102-09-0 ]
[ 118-55-8 ]

Yield	Reaction Conditions	Operation in experiment
2.88 mmol; 1.18 mmol	With C72H76N2O4P2Ti(2+)*2Cl(1-); potassium carbonate; In methanol; at 100℃; under 45004.5 Torr; for 8h;Autoclave;Catalytic behavior;	Direct synthesis of DPC from phenol and carbon dioxidewas carried out in a teflon-lined stainless steel autoclavereactor (100 ml). Methanol (0.37 mol), phenol (0.11 mol),catalyst (2.1 mmol), and K2CO3 (1.4 mmol) were charged into the reactor. The reactor was purged with carbon dioxideto remove air, and then it was pressurized up to 30bar using carbon dioxide. After heating the reactor to thereaction temperature (70-110 C) with constant stirring(600 rpm), the autoclave was additionally pressurized upto reaction pressure (50-90 bar) using carbon dioxide. Catalyticreaction was conducted for 8 h. After the reaction,the reactor was cooled to room temperature and depressurized.Reaction products were sampled and analyzed witha gas chromatograph (HP 5890 II) equipped with a flameionization detector (FID).

Reference： [1]Chemistry Letters,2006,vol. 35,p. 784 - 785
[2]Kinetics and Catalysis,2010,vol. 51,p. 359 - 363
[3]Kinetics and Catalysis,2010,vol. 51,p. 359 - 363
[4]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 8353 - 8358

28
SOCl(NO_.SUB_.3) [ No CAS ]
[ 118-55-8 ]
[ 1005139-04-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Example 21 Preparation of 2-nitrooxy-benzoic acid phenyl ester To a solution of 1 mmol of <strong>[118-55-8]2-hydroxy-benzoic acid phenyl ester</strong> (synonym: phenyl salicylate) in 5 ml of dry THF at 25 C. is added 1 mmol of SOCl(NO.SUB.3) or SO(NO.SUB.3) 2. After 1 hr, Et 2O (diethyl ether) is added and the solution is washed with water, dried and evaporated. The nitrated product 2-nitrooxy-benzoic acid phenyl ester is purified and isolated by chromatography on silica gel.

Reference： [1]Patent: US2005/80021,2005,A1
[2]Patent: US2005/80024,2005,A1

29
[ 118-55-8 ]
[ 7120-43-6 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 4112 - 4114

30
[ 118-55-8 ]
[ 6329-74-4 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1895,vol. <2> 51,p. 212

31
[ 118-55-8 ]
[ 879-18-5 ]
[ 409361-61-1 ]

Yield	Reaction Conditions	Operation in experiment
31%	aluminum (III) chloride; In chloroform; at 5 - 22℃; for 57.5h;Heating / reflux;	Synthesis of 2-Hydroxy-5-(naphthalene-1-carbonyl)-benzoic acid phenyl ester The reaction vessel was a 500 ml three neck round bottom pyrex flask fitted with a 250 ML addition funnel, thermometer, a reflux condenser, and a stirrer.. aluminum chloride (7.98 g, 59.8 mmole) and 225 ML of chloroform were added into the round bottom flask and then this stirred suspension was cooled to 5 C. with an external ice-bath.. phenyl salicylate (5.83 g, 27.2 mmole) and naphthalene-1-carbonyl chloride (4.91 ML, 6.21 g, 32.6 mmole) were combined together with 130 ML of chloroform and added dropwise over a hour and half to the stirred suspension.. Upon this addition color changes were observed from colorless to light yellow then dark green and finally to dark brown.. The temperature was maintained at 5-15 C. during the addition period.. Following the addition the reaction mixture was heated to reflux for 48 hours and then allowed to stand at 22 C. for eight hours. The reaction mixture was slowly added to a stirred slurry of 50 ML of crushed ice to which 125 ML of 12N HCl had been added.. The organic layer was isolated in a 1-liter separatory funnel and was washed 5 times with distilled water.. Purity was checked on TLC (silica gel plate) and the solvent used was 1:1 ratio of CH2Cl2 and hexane.. Three spots were observed on TLC, the phenyl ester was on the top and the product spot was in the middle. Purification was achieved by using flash column chromatography on silica gel with the same solvent system described above.. There resulted 3.75 g (31%) of the desired product phenyl ester as a white solid, mp 82-84 C. 'H NMR (300 MHz, CDCl,) delta7.276 (d, J=9.0 Hz, 1H, ArH), 7.357 (d, J=8.1 Hz, 2H, ArH), 7.459 (m, 2H, ArH), 7.617 (t, 2H, ArH), 7.732 (m, 5H, ArH), 8.120 (m, TH, ArH), 8.206 (m, 3H, ArH), 8.903 (d, J=2.1 Hz, 1H, ArH), 11.254 (s, 1H, OH, D2O exchangeable) IR (KBr) v 1652.9, 1566.1, 1199.65 cm-1.
	With hydrogenchloride;aluminium trichloride; In chloroform;	Synthesis of 2-Hydroxy-5-(Naphthalene-1-carbonyl)-benzoic Acid Phenyl Ester The reaction vessel was a 500 ml three neck round bottom pyrex flask fitted with a 250 mL addition funnel, thermometer, a reflux condenser, and a stirrer. Aluminum chloride (7.98g, 59.8 mmole) and 225 mL of chloroform were added into the round bottom flask and then this stirred suspension was cooled to 5 C. with an external ice-bath. Phenyl salicylate (5.83 g, 27.2 mmole) and naphthalene-l-carbonyl chloride (4.91 mL, 6.21 g, 32.6 mmole) were combined together with 130 mL of chloroform and added dropwise over a hour and half to the stirred suspension. Upon this addition color changes were observed from colorless to light yellow then dark green and finally to dark brown. The temperature was maintained at 5-15 C. during the addition period. Following the addition the reaction mixture was heated to reflux for 48 hours and then allowed to stand at 22 C. for eight hours. The reaction mixture was slowly added to a stirred slurry of 50 mL of crushed ice to which 125 mL of 12N HCl had been added. The organic layer was isolated in a 1-liter separatory funnel and was washed 5 times with distilled water. Purity was checked on TLC (silica gel plate) and the solvent used was 1:1 ratio of CH2Cl2 and hexane. Three spots were observed on TLC, the phenyl ester was on the top and the product spot was in the middle. Purification was achieved by using flash column chromatography on silica gel with the same solvent system described above. There resulted 3.75 g (31%) of the desired product phenyl ester as a white solid, mp 82-84 C. 'H NMR (300 MHz, CDCI,) delta7.276 (d, J=9.0 Hz, 1H, ArH), 7.357 (d, J=8.1 Hz, 2H, ArH), 7.459 (m, 2H, ArH), 7.617 (t, 2H, ArH), 7.732 (m, 5H, ArH), 8.120 (m, TH, ArH), 8.206 (m, 3H, ArH), 8.903 (d, J=2.1 Hz, 1H, ArH), 11.254 (s, 1H, OH, D2O exchangeable) IR (KBr) v 1652.9, 1566.1, 1199.65 cm-1.

Reference： [1]Patent: US6407288,2002,B1 .Location in patent: Page column 6-7
[2]Patent: US2002/65322,2002,A1

32
[ 118-55-8 ]
[ 95-53-4 ]
[ 7133-56-4 ]
[ 108-95-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,2,4-Trichlorobenzene; for 0.5h;Heating / reflux;	Phenol was distilled from a boiling mixture of phenyl salicylate (42.8 gm, 0.20 mol), 2-toluidine (26.7 gm, 0.25 mol), and 1,2,4-trichlorobenzene (41 mL) as described in the literature procedure (Organic Syntheses, Coll. Vol. 3, 765). The cooled product mixture was transferred to an 250 mL Erlenmeyer flask and boiled with hexanes (75 mL) for 30 minutes. The solid product was isolated from the hot mixture by vacuum filtration. The solid was washed with more hexanes until the filtrate was colorless. Drying gave the pure 2'-methyl-salicylanilide (41 gm, 90%) as an off-white solid.

Reference： [1]Patent: US6664427,2003,B1 .Location in patent: Page column 15

33
[ 118-55-8 ]
[ 124-63-0 ]
[ 109219-36-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In toluene; at 0 - 37℃; for 14h;	Example 7: Preparation of mesylate of formula (V) 100 g (467 mmol) of phenyl salicylate (VI) and 54.5 g (476 mmol) of methanesulfonyl chloride are reacted in 500 ml of toluene, under stirring. The solution is cooled to about 0-5C and 48.7 g (481 mmol) of triethylamine are dropped therein in about 15 minutes. The reaction temperature raises to about 37C. Afterwards the mixture is stirred at about 20-25C for 10-14 hours, monitoring the reaction by NMR and/or HPLC. Finally the solution is diluted with 500 ml of water. The formed precipitate is filtered. The organic filtrate is separated and evaporated under vacuum. The residue is combined with the precipitate and dried under vacuum at 60C for about 3 hours, thereby obtaining 130 g of product. IH NMR: (CDC13) : 8 ppm: 3.3 ppm (s, 3H); 7.2 ppm (M, 3H) ; 7.4 ppm (M, 4H); 7.6 (t, 1H); 8.2 (d, 1H).

Reference： [1]Patent: WO2004/63173,2004,A1 .Location in patent: Page 14

34
[ 6298-19-7 ]
[ 118-55-8 ]
[ 120-82-1 ]
[ 14470-90-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol;	Reference Example 189 Pyrido[2,3-b][1,4]benzoxazepin-6(5H)-one A mixture of 21.4 g of phenyl salicylate, 25.71 g 3-amino-2-chloropyridine and 20 ml of 1,2,4-trichlorobenzene is refluxed for 1 hour under argon and the liberated phenol and HCl simultaneously distilled (from the refluxing mixture) and collected in a solution of 1N NaOH. The hot mixture is poured into 200 ml of ethanol and the precipitated solid collected by filtration. The solid is washed with ethanol and dried Recrystallization from methanol--DMF (6:1) gives 6.0 g of product, m.p. 268-270 C.

Reference： [1]Patent: US5849735,1998,A

36
[ 17102-64-6 ]
[ 118-55-8 ]
(2E,4E)-2,4-hexadienyl salicylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%		In a Schlenk tube under argon, (E,E)-2,4-hexadien-1-ol (4.3 g, 44 mmol) is diluted with 50 ml anhydrous THF. At -20, butyllithium 1.6M in hexane (27.5 ml, 44 mmol) is added dropwise over 10 min. The mixture is allowed to reach 20 within 20 minutes.A solution of phenyl salicylate (9.4 g, 44 mmol) in 50 ml anhydrous THF is added over 10 min. After 15 hours, the reaction mixture is poured onto 500 ml ice water. Decantation, extraction of the aqueous phase with 3×50 ml diethyl ether, washing of the combined organic phases with brine, drying and solvent evaporation leaves a crude oil. The product is recrystallized from pentane at -20. Yield 4.4 g (46%).1H-NMR: 10.78 (s, 1H); 7.85 (dd, J=2; 8, 1H); 7.44 (dt, J=2; 8, 1H); 6.97 (d, J=8.5, 1H); 6.86 (t, J=8, 1H); 6.34 (dd, J=11; 15, 1H); 6.08 (dd, J=10; 15, 1H); 5.75 (m, 2H); 4.84 (d, J=6.5, 2H); 1.77 (d, J=7, 3H).13C-NMR: 170.0 (s); 161.7 (s); 135.7 (d); 135.6 (d); 131.9 (d); 130.3 (d); 130.0 (d); 122.9 (d); 119.1 (d); 117.5 (d); 112.5 (s); 65.8 (t); 18.2 (q).
46%		In a Schlenk tube under argon, (E,E)-2,4-hexadien-l-ol (4.3 g, 44 mmol) is diluted with 50 ml anhydrous THF. At -20, butyllithium 1.6M in hexane (27.5 ml, 44 mmol) is added dropwise over 10 min. The mixture is allowed to reach 20 within 20 minutes. A solution of phenyl salicylate (9.4 g, 44 mmol) in 50 ml anhydrous THF is added over 10 min. After 15 hours, the reaction mixture is poured onto 500 ml ice water. Decantation, extraction of the aqueous phase with 3x50 ml diethyl ether, washing of the combined organic phases with brine, drying and solvent evaporation leaves a crude oil. The product is recrystallized from pentane at -20. Yield 4.4g (46%). <n="9"/>1H-NMR: 10.78 (s, IH); 7.85 (dd, J=2; 8, IH); 7.44 (dt, J=2; 8, IH); 6.97 (d, J=8.5,IH); 6.86 (t, J=8, IH); 6.34 (dd, J=I l; 15, IH); 6.08(JJ, J=IO; 15, IH); 5.75 (m, 2H); 4.84 (J, J=6.5, 2H); 1.77 (J, J=7, 3H).13C-NMR:170.0 (s); 161.7 (s); 135.7 (J); 135.6 (J); 131.9 (J); 130.3 (J); 130.0 (J); 122.9 (J); 119.1 (J); 117.5 (J); 112.5 (s); 65.8 (t); 18.2 f°).

Reference： [1]Patent: US2008/274944,2008,A1 .Location in patent: Page/Page column 3
[2]Patent: WO2007/57810,2007,A1 .Location in patent: Page/Page column 7-8

37
[ 13509-27-8 ]
[ 118-55-8 ]
[ 616-38-6 ]
[ 108-95-2 ]
[ 102-09-0 ]

Yield	Reaction Conditions	Operation in experiment
	titanium(IV) phenoxide; under 11.2511 Torr;Heating / reflux; Industry scale;Product distribution / selectivity;	A two-stage transesterification affords 224.4 kg/h of a DPC-containing stream comprising 63.8/22.7/10.3/0.4/2.7/0.08% by weight of DPC/<strong>[13509-27-8]MPC</strong>/phenol/DMC/Ti(PhO)4/salol. This stream is worked up in a distillative refinery composed of a first distillation column (fine distillation) with vaporous sidestream withdrawal (K3) and a sidestream column (K4) according to FIG. 2.1. In addition, 1.3 kg/h of a vaporous mixture from a residue concentration comprising 99.6% by weight of DPC are fed in at the bottom of the column K3.The fine distillation (K3) consists of four sections, an upper rectifying section with 2 theoretical plates, a lower rectifying section with 12 theoretical plates, an upper stripping section with 10 theoretical plates and a lower stripping section with 9 theoretical plates. The condensation of the vapors emerging at the top of the column in the top condenser (K3C1) and the partial evaporation of the liquid effluxing from the lower stripping section (K3AT2) in the evaporator K3E1 for the bottom product are each effected in one stage.The column is operated at a top pressure of 15 mbar and a reflux ratio of 0.7.This affords, as distillate (2), a stream comprising 69.9/28.3/1.2/0.5% by weight of <strong>[13509-27-8]MPC</strong>/phenol/DMC/DPE. Below the upper rectifying section K3VT1, 0.02 kg/h of liquid are withdrawn for the purpose of discharge of high boilers in the sidestream (4). In addition, below the upper rectifying section K3VT1, 192.8 kg/h of a vaporous sidestream (6) comprising 99.9% by weight of DPC are withdrawn. The bottom product (3) obtained is 20.8 kg/h of a mixture comprising 69.8/29.6/0.5% by weight of DPC/Ti(PhO)4/salol. A substream of the bottom product, whose amount corresponds to 10% based on the total amount of the bottom product (3), is sent to a residue concentration (K3RA), consisting of a thin-film evaporator (K3E2). The remaining bottom product (24) is recycled back to the two-stage transesterification to prepare the DPC-containing stream (1). This reduces the catalyst loss by 90%.The vaporous sidestream (6) is sent to a sidestream column K4. This possesses only a rectifying section K4VT1 with 9 theoretical plates.The sidestream column K4 is operated under the same conditions as the fine distillation in the first distillation column K3 and at a reflux ratio of 0.5.The vapors (7) emerging at the top of the sidestream column K4 are condensed in a two-stage condensation in the condensers K4C1-N, the heat of condensation being used either to generate steam or to heat other process parts in the DPC preparation.This affords a distillate comprising 99.93% by weight of DPC and only 600 ppm of salol. The liquid 9 effluxing at the top of the sidestream column is sent to the fine distillation in the first distillation column K3 above the lower stripping section K3AT2.; Example 2DPC Purification in a Dividing Wall Column with Liquid Sidestream WithdrawalFor this example, a dividing wall column according to FIG. 3.1 is used. The dividing wall column K3 consists of a rectifying section with 2 sections. The upper section K3VT1 has a separating performance of 2 theoretical plates, the section K3VT2 below it a separating performance of 12 theoretical plates. Below the upper rectifying section K3VT1 there is the possibility of withdrawing a liquid stream (4) to discharge diphenyl ether.Below the rectifying section, the column is partitioned by a vertical dividing wall T. On the withdrawal side and feed side of this dividing wall are in each case disposed at least 2 sections. The feed (1) is introduced on the feed side of the dividing wall. A liquid withdrawal of the purified diphenyl carbonate (5) is effected on the withdrawal side.The upper section K3TLO disposed on the feed side of the dividing wall serves for the removal of high boilers which are present in the feed (1). The lower section of the feed side K3TLU serves for the removal of low boilers which are present in the feed (1). The upper section K3TRO disposed on the withdrawal side of the dividing wall serves for the removal of low boilers which are present in the liquid stream (15) emerging from the rectifying section. The lower section of the withdrawal side K3TRU serves for the removal of high boilers which are present in the vapor stream (17) emerging from the stripping section.The stripping section K3AT1 has a separating performance of 14 theoretical plates and serves for the concentration of the high boilers.The vapor (10) emerging from the rectifying section is condensed in a condenser K3C1-N and introduced partly as reflux (11) back to the column. The liquid (12) effluxing from the stripping section is evaporated partly in an evaporator K3E1-N.The column is operated at a top pressure of 15 mbar.The feed rate (1) to the column K3 is 236.6 kg/h. Present therein are 62.8/24.2/9.8/0.4/0.1/0.0312.6% by weight of DPC/<strong>[13509-27-8]MPC</strong>/phenol/DMC/DPE/salol/Ti(PhO)4. The distillate (2) obtained is 81.8 kg/h of a mixture comprising 69.9/28.4/1.15/0.05/0.5% by weight of <strong>[13509-27-8]MPC</strong>/p...

Reference： [1]Patent: US2009/137832,2009,A1 .Location in patent: Page/Page column 11-12

38
[ 118-55-8 ]
[ 95-84-1 ]
[ 35875-76-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	at 200℃; for 1.5h;Inert atmosphere;	A mixture of 2-amino-p-cresol (10.0 g, 0.081 mole) and phenyl salicylate (17.4 g, 0.08 mole) was heated under nitrogen atmosphere in an oil bath at 200 0C for 1 V2 h. To the cooled reaction mixture ethanol was added and the product filtered off under suction. The product was dried under vacuum at 75 0C, and then purified by column chromatography (dichloromethane). The eluent containing the product was concentrated and ethanol added to the residue to give a bright white crystalline solid. The product was suction filtered and dried under vacuum at 75 0C. Yield 7.4 g (40 %). M. p 138 0C (DSC, onset). Elemental analysis: Found, C 74.62, H 4.86 and N 6.32 %. C14HnNO2 requires C 74.65, H 4.92 and N 6.22%.

Reference： [1]Patent: WO2010/20352,2010,A1 .Location in patent: Page/Page column 47

39
[ 118-55-8 ]
[ 106-95-6 ]
[ 93011-75-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 2961 - 2967

40
[ 201230-82-2 ]
[ 108-95-2 ]
[ 102-09-0 ]
[ 118-55-8 ]

Reference： [1]Electrochimica Acta,2011,vol. 56,p. 2926 - 2933

41
[ 1121-22-8 ]
[ 118-55-8 ]
trans-1-amino-2-(2-hydroxybenzamide)cyclohexane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In isopropyl alcohol; at 20℃;	General procedure: A solution of phenyl salicylate (2.13 g, 9.9 mmol) in 2-propanol (30 mL) was added to a 2-propanol solution (10 mL) containing 1,2-diamino-2-methylpropane (0.93 g, 10.6 mmol) dropwise with stirring. The mixture was stirred overnight at room temperature. The resulting white precipitate was collected by filtration, washed with 2-propanol and diethyl ether, and dried in vacuo.

Reference： [1]Chemistry Letters,2011,vol. 40,p. 696 - 698
[2]Inorganica Chimica Acta,2013,vol. 399,p. 131 - 137

42
[ 118-55-8 ]
[ 78-90-0 ]
[ 688315-69-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	In isopropyl alcohol; at 20℃;	General procedure: A solution of phenyl salicylate (2.13 g, 9.9 mmol) in 2-propanol (30 mL) was added to a 2-propanol solution (10 mL) containing 1,2-diamino-2-methylpropane (0.93 g, 10.6 mmol) dropwise with stirring. The mixture was stirred overnight at room temperature. The resulting white precipitate was collected by filtration, washed with 2-propanol and diethyl ether, and dried in vacuo.

Reference： [1]Chemistry Letters,2011,vol. 40,p. 696 - 698
[2]Inorganica Chimica Acta,2013,vol. 399,p. 131 - 137
[3]Dalton Transactions,2015,vol. 44,p. 3430 - 3438

43
[ 118-55-8 ]
[ 811-93-8 ]
[ 688315-68-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	In isopropyl alcohol; at 20℃;	A solution of phenyl salicylate (2.13 g, 9.9 mmol) in 2-propanol (30 mL) was added to a 2-propanol solution (10 mL) containing 1,2-diamino-2-methylpropane (0.93 g, 10.6 mmol) dropwise with stirring. The mixture was stirred overnight at room temperature. The resulting white precipitate was collected by filtration, washed with 2-propanol and diethyl ether, and dried in vacuo. Yield: 1.54 g (76%). 1H NMR (CD3OD, 22 C): delta 1.27 (s, 6H, -CH3), 3.46 (s, 2H, -CH2-), 6.70 (ddd, J = 1.1, 7.1, and 8.0 Hz, 1H, aryl-H), 6.81 (dd, J = 8.3 and 0.8 Hz, 1H, aryl-H), 7.27 (ddd, J = 8.5, 7.0, and 1.8 Hz, 1H, aryl-H), 7.82 (dd, J = 7.8 and 1.8 Hz, 1H, aryl-H).

Reference： [1]Chemistry Letters,2011,vol. 40,p. 696 - 698
[2]Inorganica Chimica Acta,2013,vol. 399,p. 131 - 137
[3]Dalton Transactions,2019,vol. 48,p. 8617 - 8622

44
[ 3731-52-0 ]
[ 118-55-8 ]
[ 5620-22-4 ]

Yield	Reaction Conditions	Operation in experiment
64%	at 190 - 210℃; for 1.5h;

Reference： [1]Location in patent: experimental part Petrlikova, Eva; Waisser, Karel; Palat Jr., Karel; Kunes, Jiri; Kaustova, Jarmila [Chemical Papers, 2011, vol. 65, # 1, p. 52 - 59]

45
[ 20439-47-8 ]
[ 118-55-8 ]
(1R,2R)-trans-1-amino-2-(2-hydroxybenzamide)cyclohexane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; at 20℃;	General procedure: A solution of phenyl salicylate (2.13 g, 9.9 mmol) in 2-propanol (30 mL) was added to a 2-propanol solution (10 mL) containing 1,2-diamino-2-methylpropane (0.93 g, 10.6 mmol) dropwise with stirring. The mixture was stirred overnight at room temperature. The resulting white precipitate was collected by filtration, washed with 2-propanol and diethyl ether, and dried in vacuo.

Reference： [1]Inorganica Chimica Acta,2013,vol. 399,p. 131 - 137

46
[ 78-90-0 ]
[ 118-55-8 ]
[ 1334305-20-2 ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; at 20℃;	General procedure: A solution of phenyl salicylate (2.13 g, 9.9 mmol) in 2-propanol (30 mL) was added to a 2-propanol solution (10 mL) containing 1,2-diamino-2-methylpropane (0.93 g, 10.6 mmol) dropwise with stirring. The mixture was stirred overnight at room temperature. The resulting white precipitate was collected by filtration, washed with 2-propanol and diethyl ether, and dried in vacuo.

Reference： [1]Inorganica Chimica Acta,2013,vol. 399,p. 131 - 137

47
[ 118-55-8 ]
[ 89-73-6 ]

Reference： [1]Oriental Journal of Chemistry,2012,vol. 28,p. 1841 - 1844

48
[ 118-55-8 ]
[ 100-51-6 ]
[ 88815-27-4 ]

Yield	Reaction Conditions	Operation in experiment
46%	With tert.-butylhydroperoxide; copper diacetate; In water; dimethyl sulfoxide; at 80℃; for 20h;Sealed tube;	General procedure: To an oven-dried sealed tube charged with 2-hydroxyacetophenone (1a) (40.8mg, 0.3mmol, 1.0equiv), Cu(OAc)2 (2.7mg, 0.015mmol, 5mol%), and TBHP (70% in water) (0.16mL, 1.2mmol, 4.0equiv) in DMSO (1mL, 0.3M) was added benzyl alcohol (2a) (65.4mg, 0.6mmol, 2equiv). The reaction mixture was allowed to stir at 80C for 20h. After cooling at room temperature, the reaction mixture was evaporated onto silica gel. Purification of the product by column chromatography (SiO2: n-hexanes/EtOAc=40:1) provided 3a (50.5mg) in 70% yield 4.2.12 Phenyl 2-(benzoyloxy)benzoate (3l) White solid; mp 68-71 C; Rf=0.40 (n-hexanes/EtOAc=6:1); 1H NMR (700 MHz, CDCl3) delta 8.26 (d, J=7.8 Hz, 1H), 8.20 (d, J=8.2 Hz, 2H), 7.67 (t, J=7.7 Hz, 1H), 7.57 (t, J=7.5 Hz, 1H), 7.46-7.41 (m, 3H), 7.32-7.29 (m, 3H), 7.17 (t, J=7.4 Hz, 1H), 7.07 (d, J=8.4 Hz, 2H); 13C NMR (175 MHz, CDCl3) delta 165.2, 162.9, 151.1, 150.4, 134.4, 133.5, 132.2, 130.3, 129.3, 129.2, 128.4, 126.2, 125.8, 124.1, 123.0, 121.5; IR (KBr) nu 2921, 1742, 1605, 1484, 1451, 1265, 1206, 1192, 1112, 1078, 1058, 1023 cm-1; HRMS (EI) calcd for C20H14O4 [M]+ 318.0892, found 318.0883.

Reference： [1]Tetrahedron,2013,vol. 69,p. 9391 - 9397

49
[SnO₂AlB(isopropoxide)₄] [ No CAS ]
[ 118-55-8 ]
[SnO₂AlB(isopropoxide)₃(phenyl salicylate)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In benzene; at 100℃; for 5.5h;Reflux; Inert atmosphere;	General procedure: [SnO2AlB(OPri)4] was prepared in laboratory by reported methods [29-31]. The complex [SnO2AlB(OPri)4] (0.434 g, 1.021 mmol) and methyl salicylate (0.155 g, 1.021 mmol) were refluxed in benzene (~50 mL) for 4 h at ~100 oC in a flask connected to short distillation column. The liberated isopropanol was collected continuously at 72-78 oC as a binary azeotrope of isoproponol-benzene [24]. The isopropanol in azeotrope was estimated oxidimetrically to check the completion of the reaction. The excess of the solvent was then removed at reduced pressure (45 oC/1 mm Hg) yielding a yellowish brown solid product. Similar procedure was adopted for the preparation of other derivatives of [SnO2AlB(OPri)4] with Salicylates (HRSAL), i.e. methyl salicylate (HRSAL1), ethyl salicylate (HRSAL2), phenyl salicylate (HRSAL3), phenyl ethyl salicylate (HRSAL4) in stiochiometric ratio of 1:1 and 1:2 molar ratios.

Reference： [1]Bulletin of the Chemical Society of Ethiopia,2013,vol. 27,p. 377 - 386

50
[SnO₂AlB(isopropoxide)₄] [ No CAS ]
[ 118-55-8 ]
[SnO₂AlB(isopropoxide)₂(phenyl salicylate)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.5%	In benzene; at 100℃; for 11h;Reflux; Inert atmosphere;	General procedure: [SnO2AlB(OPri)4] was prepared in laboratory by reported methods [29-31]. The complex [SnO2AlB(OPri)4] (0.434 g, 1.021 mmol) and methyl salicylate (0.155 g, 1.021 mmol) were refluxed in benzene (~50 mL) for 4 h at ~100 oC in a flask connected to short distillation column. The liberated isopropanol was collected continuously at 72-78 oC as a binary azeotrope of isoproponol-benzene [24]. The isopropanol in azeotrope was estimated oxidimetrically to check the completion of the reaction. The excess of the solvent was then removed at reduced pressure (45 oC/1 mm Hg) yielding a yellowish brown solid product. Similar procedure was adopted for the preparation of other derivatives of [SnO2AlB(OPri)4] with Salicylates (HRSAL), i.e. methyl salicylate (HRSAL1), ethyl salicylate (HRSAL2), phenyl salicylate (HRSAL3), phenyl ethyl salicylate (HRSAL4) in stiochiometric ratio of 1:1 and 1:2 molar ratios.

Reference： [1]Bulletin of the Chemical Society of Ethiopia,2013,vol. 27,p. 377 - 386

51
[ 124-38-9 ]
[ 108-95-2 ]
[ 118-55-8 ]

Yield	Reaction Conditions	Operation in experiment
0.01 mmol	With C56H49CoN2O4P2(2+)*2Cl(1-); potassium carbonate; In methanol; at 100℃; under 45004.5 Torr; for 8h;Autoclave;	Direct synthesis of DPC from phenol and carbon dioxidewas carried out in a teflon-lined stainless steel autoclavereactor (100 ml). Methanol (0.37 mol), phenol (0.11 mol),catalyst (2.1 mmol), and K2CO3 (1.4 mmol) were charged into the reactor. The reactor was purged with carbon dioxideto remove air, and then it was pressurized up to 30bar using carbon dioxide. After heating the reactor to thereaction temperature (70-110 C) with constant stirring(600 rpm), the autoclave was additionally pressurized upto reaction pressure (50-90 bar) using carbon dioxide. Catalyticreaction was conducted for 8 h. After the reaction,the reactor was cooled to room temperature and depressurized.Reaction products were sampled and analyzed witha gas chromatograph (HP 5890 II) equipped with a flameionization detector (FID).
23.2%Chromat.	With tetrabutylammomium bromide; potassium carbonate; In tetrachloromethane; at 110℃; under 15001.5 - 37503.8 Torr; for 8h;Autoclave;	To a 250 mL autoclave was added 50 mmol of phenol,50 mL of CCl4, 25 mmol of K2C03,After a certain period of time, 50 mol% of ZnBr2, 17 mmol of tetrabutylammonium bromide was added,To the reaction of the introduction of pressure to 2. OMPa of carbon dioxide used to replace the tank three times the air,Heating up to 110 C,To the kettle through the carbon dioxide to the kettle pressure increased to 5. OMPa,Continue to stir the reaction 8. Oh stop stirring,The reaction mixture was cooled to room temperature and qualitatively analyzed by a gas chromatography-mass spectrometer,Quantitative analysis by gas chromatography, phenyl salicylate yield of 23. 2%.

Reference： [1]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 8353 - 8358
[2]Patent: CN105294444,2016,A .Location in patent: Paragraph 0029; 0030

52
[ 67-56-1 ]
manganese(II) perchlorate hexahydrate [ No CAS ]
[ 1334305-20-2 ]
[ 118-55-8 ]
C₂₄H₃₈Mn₂N₄O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		A solution of phenyl salicylate (276 mg, 1.29 mmol) in 2-propanol (5 mL) was added to a 2-propanol solution (3 mL) of (R)-1,2-diaminopropane (144 mg, 1.94 mmol), and the mixture was stirred for 2 d. To the resulting solution were added triethylamine(0.36 mL, 2.6 mmol) and a methanol solution (5 mL) ofMn(ClO4)26H2O (469 mg, 1.30 mmol); the mixture was further stirred at room temperature for several days. A brown precipitate,thus formed, was collected by filtration and washed with methanol (yield: ca. 70%). The crude product was recrystallized from a mixture of DMF and MeOH. Anal. Calc. for Mn2{(R)-L2Me}2(OMe)2(H2O)= C22H32Mn2N4O7: C, 46.00; H, 5.67; N, 9.75. Found (after efflorescence):C, 45.76; H, 5.37; N, 9.46%. IR (KBr disc): 1598, 1568, 1521,1451 and 756 cm-1

Reference： [1]Inorganica Chimica Acta,2016,vol. 447,p. 113 - 120

53
[ 118-55-8 ]
[ 121-92-6 ]
phenyl 2-((3-nitrobenzoyl)oxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With iodine; triethylamine; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 0.333333h;	General procedure: To a solution of iodine (0.1573 g, 0.62 mmol) in CH2Cl2 (2 mL) was added with triphenylphosphine (0.1626 g, 0.62 mmol) in one portion at 0 oC. Phenol derivative (0.45mmol) and carboxylic acid (0.41 mmol) were subsequently added into the mixture,followed by addition of triethylamine (0.17 mL, 1.23 mmol) at 0 oC. The reaction mixture was allowed to warm up to room temperature and stirred until completion of thereaction (typically within 20 min). The crude mixture was concentrated under reduced pressure then purified by column chromatography (CC) using 5-10% ethyl acetate inhexane to give the desired phenolic ester product.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2087 - 2089

54
[ 22661-87-6 ]
[ 118-55-8 ]
C₉H₁₁N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Salicylic acid-based compound (15,1eq.) Added to the reaction solvent methylene chloride, SOCl2 (3eq.) Was added dropwise to the solution. The resulting reaction mixture was reacted at 50 1h after the spin evaporated on a rotary evaporator to remove SOCl2. The resulting crude product was dissolved using methylene chloride, then added dropwise phenol (phenol, 1eq.) And triethylamine (TEA, 3eq.) In a mixture of dichloromethane. The resulting reaction mixture was stirred at r.t. 1h, quenched with water. Extracted with dichloromethane, the organic phases were dried over anhydrous magnesium sulfate. After the desiccant was filtered, the organic phase was mixed with silica gel column chromatography using silica gel, yielding intermediate 16. Intermediate 16 (1eq.) And 1,1,3,3-tetramethylguanidine (TMG, 1.5eq.) Was added the reaction solvent, N, N- dimethylformamide was stirred after 5min,JoinGuanidines (17,1.6eq.), Stirred at room temperature overnight. Completion of the reaction was quenched with water, extracted with ethyl acetate after using silica gel column chromatography to obtain benzoyl guanidine compound (18). Intermediate 16, O- benzotriazole (1eq.) - (. HBTU, 1.6eq) tetramethyluronium hexafluorophosphate, N, N- diisopropylethylamine (. DIEA, 3eq) was added Solvent N, N- dimethyl formamide. The reaction was stirred at rt for 30min, amidino compound (19,1.2eq.) Added to the reaction mixture. The reaction mixture was stirred at room temperature overnight, quenched with water. After extraction with ethyl acetate, silica gel column chromatography to obtain the amidine-benzoyl compound (20).

Reference： [1]Patent: CN105523955,2016,A .Location in patent: Paragraph 0163; 0164; 0165; 0291

55
[ 124-42-5 ]
[ 118-55-8 ]
C₉H₁₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Salicylic acid-based compound (15,1eq.) Added to the reaction solvent methylene chloride, SOCl2 (3eq.) Was added dropwise to the solution. The resulting reaction mixture was reacted at 50 1h after the spin evaporated on a rotary evaporator to remove SOCl2. The resulting crude product was dissolved using methylene chloride, then added dropwise phenol (phenol, 1eq.) And triethylamine (TEA, 3eq.) In a mixture of dichloromethane. The resulting reaction mixture was stirred at r.t. 1h, quenched with water. Extracted with dichloromethane, the organic phases were dried over anhydrous magnesium sulfate. After the desiccant was filtered, the organic phase was mixed with silica gel column chromatography using silica gel, yielding intermediate 16. Intermediate 16 (1eq.) And 1,1,3,3-tetramethylguanidine (TMG, 1.5eq.) Was added the reaction solvent, N, N- dimethylformamide was stirred after 5min,JoinGuanidines (17,1.6eq.), Stirred at room temperature overnight. Completion of the reaction was quenched with water, extracted with ethyl acetate after using silica gel column chromatography to obtain benzoyl guanidine compound (18). Intermediate 16, O- benzotriazole (1eq.) - (. HBTU, 1.6eq) tetramethyluronium hexafluorophosphate, N, N- diisopropylethylamine (. DIEA, 3eq) was added Solvent N, N- dimethyl formamide. The reaction was stirred at rt for 30min, amidino compound (19,1.2eq.) Added to the reaction mixture. The reaction mixture was stirred at room temperature overnight, quenched with water. After extraction with ethyl acetate, silica gel column chromatography to obtain the amidine-benzoyl compound (20).

Reference： [1]Patent: CN105523955,2016,A .Location in patent: Paragraph 0163; 0164; 0165; 0291

56
[ 100-47-0 ]
[ 69-72-7 ]
[ 118-55-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With thionyl chloride; at 75 - 145℃; for 4h;	In a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, 1.31 mol of benzonitrile and 1.23mol of salicylic acid were added and the solution temperature was raised to 145C. The stirring speed was controlled to 170 rpm. After 40 min, 0.23mol of thionyl chloride was added and the reaction temperature was maintianed at 138C. Then the temperature of the solution was reduced to 75C with the reaction time controlled to 4h. The reaction solution was divided into two layers. The upper layer was separated and added to 200 ml of potassium bromide solution to obtain a solid which was pulverized and washed with 500 ml of a potassium hydrogencarbonate solution having a mass fraction of 70% 6 times, calcium sulfate dehydration, mass fraction of 95% acetonitrile solution was recrystallized, in 197 g of phenyl salicylate, yield 74%.

Reference： [1]Patent: CN105601511,2016,A .Location in patent: Paragraph 0014; 0015

57
phenyl chloro oxalate [ No CAS ]
[ 118-55-8 ]
phenyl (o-phenoxycarbonylphenyl) oxalate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.2 g		This chloro oxalic acid phenyl were placed in an eggplant-shaped flask of 500cm3 together with tetrahydrofuran 100cm3.Thereto, by the dropwise addition of pyridine 6.6 g (0.08 mol) over 10 minutes,To obtain a slurry.The phenyl salicylate 18.0g (0.08 mol) and tetrahydrofuran 100cm3 placed in a beaker of 200cm3,After that was added to the above slurry,The reaction was carried out for 2 hours.After completion of the reaction,Toluene 100cm3 addition,It was hydrolyzed further by the addition of water 100cm3.Transfer the hydrolyzed 2-phase separated liquid to a separatory funnel,The water is separated.The resulting organic phase,After obtaining the two-phase separated liquid was neutralized by thoroughly mixed with a saturated aqueous sodium hydrogen carbonate solution 100 cm 3,The aqueous phase was separated.The resulting organic phase,The aqueous phase was separated after that was dehydrated by further addition of saturated sodium chloride aqueous solution 100cm3.The resulting organic phase was transferred to an Erlenmeyer flask of 500cm3,By adding magnesium sulfate 30g,It was further dehydration.After filtering off the magnesium sulfate by filtration the organic phase,The organic phase was transferred to an eggplant-shaped flask of 500cm3,Using an evaporator under reduced pressure,It was distilled tetrahydrofuran.Gradually Hexane was added to the liquid which was distilled this tetrahydrofuran,Crystals was allowed to cool to stop the addition of hexane where has been deposited.The resulting slurry was filtered under reduced pressure,Obtained white solids.The solids of the white dried under reduced pressure,To give phenyl (o-phenoxycarbonyl phenyl) oxalate (OCPO) 10.2g (0.03 mol).

Reference： [1]Patent: JP2016/20315,2016,A .Location in patent: Paragraph 0061

58
[ 66003-76-7 ]
[ 69-72-7 ]
[ 118-55-8 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 5250 - 5262

59
[ 118-55-8 ]
[ 6476-32-0 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 13809 - 13813
Angew. Chem.,2017,vol. 129,p. 13997 - 14001,5

60
[ 118-55-8 ]
C₁₃H₉Cl₃O₃Se [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With selenium tetrachloride; In tetrahydrofuran; at 20℃; for 1h;	General procedure: Synthetic procedure followed Scheme 1. A solution of SeCl4 (5?mmol, 1.107?g) in THF (10?mL) was added to a solution of salicyloylamines (5?mmol) in THF (10?mL) and the mixture was stirred for 1?h at room temperature (RT). Then water (100?mL) was added to the reaction mixture, followed by stirring at RT for additional 24?h. White seleninic acid (3) precipitated was filtered, washed with THF (3 x 30?mL) and dried in air. When hydrazine hydrate (2?mmol, 0.2?mL) was added to a solution of 3 (2?mmol) in THF (10?mL) and the mixture was stirred at RT for 24?h followed by evaporation of THF to produce yellow to orange diselenide (4).

Reference： [1]Journal of Organometallic Chemistry,2018,vol. 862,p. 86 - 94

61
[ 7732-18-5 ]
[ 142-71-2 ]
[ 118-55-8 ]
[ 111-40-0 ]
Cu⁽¹⁺⁾*C₁₁H₁₆N₃O₂^(1-)*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%		[CuL1H2O] (1). A mixture of phenyl salicylate (2.14 g, 1 x 102mol) and diethylenetriamine (1.03 g, 1 102 mol) was refluxed for 30 min and then cooled to room temperature with stirring. The resulting pasty product was dissolved in acetone (50 mL). Copper acetate (2.0 g, 1 102 mol) and piperidine (2 mL, 2 102mol) were added and the solution was refluxed and stirred for 1 h. The resulting violet precipitate was filtered off from the cooled solution and dried. Yield: 0.9 g (31%). Anal. Calc. for C11H15CuN3O2(284.80): C, 46.39; H, 5.31; N, 14.75. Found: C, 46.03; H, 5.18; N,14.48. IR (ATR): 3248s, 3103m, 2930m, 2876m, 1592m, 1558s,1520s, 1461m, 1440m, 1385s, 1324m, 1316m, 1258m, 1237w,1155m, 1145w, 1099m, 1091m, 1038m, 961w, 890w, 842w,760m, 704w, 651w.

Reference： [1]Polyhedron,2018,vol. 153,p. 158 - 162

62
[ 118-55-8 ]
[ 111-40-0 ]
[ 76274-44-7 ]

Yield	Reaction Conditions	Operation in experiment
29%		L1H2. A mixture of phenyl salicylate (2.14 g, 1 102 mol) and diethylenetriamine (1.03 g, 1 x 102 mol) was refluxed for 30 min and then cooled to room temperature with stirring. The resulting pasty product was dissolved in methanol. Addition of picric acid induced a quick precipitation that was separated by filtration.The new precipitate that appeared in the filtrate was filtered off, washed with diethyl oxide and dried. This precipitate correspondsto the picrate salt of the desired ligand. Yield: 1.3 g (29%). Anal. Calc. for C17H20N6O9 (452.38): C, 45.14; H, 4.46; N, 18.58. Found: C,44.81; H, 4.33; N, 18.23. 1H NMR (250 MHz, 20 C, dmso d6): d 3.22(m, 4H, CH2N), 3.39 (m, 2H, CH2N), 3.61 (m, 2H, CH2N), 6.90 (t, J = 7Hz, 1H, C(5)H), 6.91 (d, J = 7 Hz, 1H, C(3)H), 7.41 (t, J = 7 Hz, 1H, C(4)H), 7.81 (d, J = 7 Hz, 1H, C(6)H), 8.10 (l, 3H, NH), 8.59 (s, 2H,CH pic), 8.92 (t, J = 6 Hz, 1H, OCNH), 12.20 (l, 2H, OH). 13C{1H}NMR (62.896 MHz, 20 C, dmso d6): d 35.67 (s, CH2NH), 36.16 (s,CH2NH), 44.65 (s, CH2NH2), 47.36 (s, CH2NHCO), 115.89 (s, ArC(1)H), 117.75(s, ArC(3)), 119.17 (s, ArC(5)H), 124.90 (s, picCpNO2),125.72 (s, picCH), 128.74 (s, ArC(6)H), 134.35 (s, ArC(4)), 142.22(s, picCoNO2), 159.94 (s, ArC(2)OH), 161.32 (s, picCO), 169.80 (s,OCNH).

Reference： [1]Polyhedron,2018,vol. 153,p. 158 - 162

63
sulfurisocyanatidic chloride [ No CAS ]
[ 118-55-8 ]
C₁₄H₉NO₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 140℃; for 18h;	General procedure: For the synthesis of 2, the solution of sulfurisocyanatidic chloride (7.2mmol) in 20mL toluene was added to the solution of 1 (6.0mmol) in 20mL toluene dropwise at room temperature. The reactant was heated to 140C and then the reaction proceeded for 18h under reflux. Subsequently, the mixture was cooled down to room temperature and remaining sulfurisocyanatidic chloride was removed under reduced pressure, together with the solvent. Without further purification, the resulting yellow oil 2 was dissolved in 10mL anhydrous acetonitrile and after that it was added slowly to 5mmol of 3, which was also dissolved in 10mL anhydrous acetonitrile beforehead in ice bath. After stirring for 24hat room temperature, acetonitrile was removed under reduced pressure and saturated sodium bicarbonate was added to product 4. Product 5 precipitated easily and it was further purified by recrystallization from petroleum ether/acetone in 1:1 ratio in high yields. 15% hydrochloric acid was added to aqueous solution of 5 under stirring and corresponding acidified product 4 precipitated out easily in high yields.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 162,p. 348 - 363

64
[ 118-55-8 ]
[ 920-46-7 ]
[ 33374-44-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In dichloromethane; at -15 - 20℃; for 20h;Inert atmosphere;	4.28 g (20 mmol) of phenyl salicylate and 3.34 g (33 mmol) of triethylamine were dissolved in 50 mL of dry CH2C12 in a 100 mL three-necked round-bottomed flask, thoroughly purged with Ar and cooled to -15 C. Meanwhile, 2.30 g (22 mmol) of freshly distilled methacryloyl chloride were dissolved in 20 mL of dry CH2C12, also purged with Ar and then added dropwise to the reaction mixture within 1 h without exceeding a temperature of 0 C. When the addition was completed, the reaction mixture was stirred for 1 h at a temperature below 0 C and then slowly warmed up to room temperature and stirred for 18 h, whereafter a precipitate had formed, which was removed by filtration. The filtrate was washed twice with water, three times with aqueous 10% HC1, and twice with brine. Then the organic layer was dried over Na2S04, filtered through a silica bed, stabilized with 250 ppm of BHT, and then the solvent was evaporated. The resulting white crystals were recrystallized from diethyl ether to yield 5.10 g (90%) of Refl. mp: 99-100 C; *H NMR (200 MHz, CDC13; d, ppm): 8.22 (d, 1H; Ar-H), 7.63 (t, 1H; Ar-H), 7.37 (m, 3H; Ar-H), 7.27-7.11 (m, 4H; Ar-H), 6.36 (s, 1H; ^Tb), 5.70 (m, 1H; =(), 2.03 (s, 3H; CH2=CH2- CTh); APT 13C NMR (50.3 MHz, CDC13; d, ppm): 166.0 (C4), 163.2 (C4), 151.3 (C4), 150.7 (C4), 135.6 (C4), 134.5 (C3), 132.4 (C3), 129.6 (C3), 127.9 (C2), 126.2 (C3), 126.1 (Cl), 124.2 (C3), 123.1 (C4), 121.8 (C3), 18.5 (Cl).

Reference： [1]Patent: WO2019/213588,2019,A1 .Location in patent: Paragraph 0164-0165

65
[ 118-55-8 ]
[ 80-08-0 ]
[ 25591-55-3 ]