30131-16-9|4-(4-Phenylbutoxy)benzoic acid| Ambeed

Structure of 30131-16-9

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Quality Control of [ 30131-16-9 ] Purity: 97% SDS Specification

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Product Details of [ 30131-16-9 ]

CAS No. :	30131-16-9
Formula :	C₁₇H₁₈O₃
M.W :	270.32
SMILES Code :	O=C(O)C1=CC=C(OCCCCC2=CC=CC=C2)C=C1
MDL No. :	MFCD07787608
Boiling Point :	No data available
InChI Key :	XWCWFMQMZZPALR-UHFFFAOYSA-N
Pubchem ID :	11043825

Safety of [ 30131-16-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 30131-16-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	12
Fraction Csp3	0.24
Num. rotatable bonds	7
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	78.8
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.86
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	4.99
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.79
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.55
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.91
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.82

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.64
Solubility	0.00617 mg/ml ; 0.0000228 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-5.71
Solubility	0.000531 mg/ml ; 0.00000197 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.65
Solubility	0.000608 mg/ml ; 0.00000225 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.41 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.9

Application In Synthesis of [ 30131-16-9 ]

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

Downstream synthetic route of [ 30131-16-9 ]

[ 30131-16-9 ] Synthesis Path-Downstream 1~35

1
[ 30131-16-9 ]
[ 110683-22-2 ]
[ 103177-37-3 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 84 - 91.

2
[ 30131-16-9 ]
[ 110683-20-0 ]
[ 103176-67-6 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 84 - 91.

3
[ 136450-05-0 ]
[ 30131-16-9 ]

Yield	Reaction Conditions	Operation in experiment
98.7%	With water; potassium hydroxide; at 80℃; for 3h;	(1) thermal reaction: to the base KOH, adding amount is 47.2g (content is 95.0%, 0 . 8mol), the reaction temperature is 120 C, the reaction time is 3h, other operation with the embodiment 1; (2) condensation reaction: with the embodiment 1, as shown in formula (IV) of the obtained 4-( benzene butoxy) benzoate object nitrile oil 101.9g, the purity of 96.2% (GC), molar yield of 97.5% (to 4-chlorobenzene nitrile idea); (3) alcoholysis reaction: the above-mentioned is obtained by reacting 4-( benzene butoxy) nitrile oil -benzoate (101.9g, the purity of 96.2%, 0 . 390mol) adding 713.3g water-free methanol, the reaction temperature to 60 C, alcoholysis reaction time to 6h, other operation with the embodiment 5, is shown as formula (V) as shown in 4-( benzene butoxy) benzoic acid armor ester oil objects 110.5g, the purity of 98.8% (GC), the molar yield 98.4% (to 4-( benzene butoxy) benzonitrile nitrile idea); (4) the hydrolysis reaction of the alcoholysis after: the above-mentioned reaction of the 4-( benzene butoxy) benzoic acid ethyl ester oil objects (116.3g, the purity of 98.8%, 0 . 384mol) into 200 ml water, an aqueous solution of solid KOH adjusted to pH 14, the temperature is increased to 80 C hydrolysis reaction 3h after cooling to room temperature, adjusted by adding concentrated hydrochloric acid to pH 2 after precipitating a large amount of white solid, filtering, the water washing of the filter cake to neutral pH, hot air drying, to obtain the formula (I) indicated by 4-( benzene butoxy) benzoic acid white crystal 79.1g, melting point 130-131C, molar yield 98.7% (4-( benzene butoxy) benzonitrile nitrile idea), purity 99.3% (HPLC).
92%		18B 4-(4-Phenylbutoxy)benzoic acid Following the process described in example 10 (point B), starting from methyl 4-(4-phenylbutoxy)benzoate, the title compound was prepared which was purified by digestion in ethyl ether (92% yield). 1 H N.M.R. (300 MHz, CD3 OD) delta ppm: 1.81 (m, 4H); 2.68 (t, 2H); 4.01 (t, 2H); 6.90 (d, 2H); 7.16-7.31 (sc, 5H); 7.97 (d, 2H).
88%	With sodium hydroxide; In water; at 95℃; for 3h;	To 180 g of methyl p-butoxybutyrate, 300 mL of water,47.4g (2eq) of sodium hydroxide is heated to 95 C,After 3 hours of reaction, the temperature was lowered to 30 C and 400 mL of water was added to heat to 55 C.Slowly add 6N hydrochloric acid to adjust the pH to 4,Use 1N hydrochloric acid dropwise to adjust the pH to 3.2 and filter while hot.The filter cake was washed with 50 mL of hot water at 55 C, and the solid was dried under reduced pressure below 40 C to obtain a crude product.The crude product was added with 3 volumes of isopropanol and heated to reflux for 0.5 h, and then cooled to 60 C over 2 h.Solids precipitated, and kept at 60 C for 1 h.Then cool down to 30 in 3h, cool down to 5 in 0.5h, then crystallize for 2h and suction filter.The filter cake was rinsed with 20 mL of isopropyl alcohol at 5 C.A white solid was obtained and dried under reduced pressure at 40 C.White crystalline solid p-phenylbutoxybenzoic acid was obtained in a yield of 88%.

References: [1]Patent: CN103588638,2016,B .Location in patent: Paragraph 0073-0078.
[2]Patent: US5990142,1999,A .
[3]Patent: CN110357772,2019,A .Location in patent: Paragraph 0070; 0073; 0078; 0081.
[4]New Journal of Chemistry,2017,vol. 41,p. 4672 - 4679.
[5]ChemMedChem,2018,vol. 13,p. 2530 - 2545.
[6]Journal of Medicinal Chemistry,1988,vol. 31,p. 84 - 91.

Yield	Reaction Conditions	Operation in experiment
		Production Example 1 Production of 4-(4-phenyl-1-butoxy)benzoic acid To 100 ml of methyl isobutyl ketone were added 17.6 g of methyl p-hydroxybenzoate, 23.0 g of 4-phenyl-1-bromobutane and 22 g of anhydrous potassium carbonate. The mixture was heated under reflux for 10 hours for the reaction, after which 65 g of 20% sodium hydroxide was added thereto. The mixture was heated under reflux for 6 hours for the reaction. After completion of the reaction, 300 ml of water was added thereto. The reaction mixture was separated into an aqueous layer and an organic layer. After removal of the organic layer, the aqueous layer was washed twice with 50 ml of toluene. The resultant aqueous layer was made acidic by the addition of 48% sulfuric acid, and then extracted with 200 ml of toluene, which afforded a solution of 4-(4-phenyl-1-butoxy)benzoic acid in toluene. The product content in the solution was measured and the yield was determined to be 93%.

5
[ 4830-93-7 ]
[ 30131-16-9 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 84 - 91.
[2]Patent: CN110357772,2019,A .

6
[ 99-76-3 ]
[ 30131-16-9 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 84 - 91.
[2]New Journal of Chemistry,2017,vol. 41,p. 4672 - 4679.
[3]ChemMedChem,2018,vol. 13,p. 2530 - 2545.

7
[ 30131-16-9 ]
[ 108807-05-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In toluene;	Production Example 2 Production of 3[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone To the solution of <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong> in toluene obtained in Production Example 1, 12.9 g of thionyl chloride was added dropwise at room temperature, and the mixture was stirred at 40 C. for 30 minutes. After completion of the reaction, excess thionyl chloride and toluene were removed under reduced pressure, which afforded 4-(4-phenyl-1-butoxy)benzoyl chloride.
	With thionyl chloride; In ISOPROPYLAMIDE; at 0℃;	<strong>[30131-16-9]4-(4-phenylbutoxy)benzoic acid</strong> (29.1 g; 1.1 equivalent ratio; prepared according to the method disclosed in US Pat. No. 4,780,469) was dissolved in 80 ml dimethylacetamide (DMAC, Aldrich) at 00C and then thionyl chloride (14.2 g, 1.2 equivalent ratio, Aldrich) was gradually added to the solution. After the mixture solution was stirred for 10 min at 00C, the mixture of 8-amino-4-oxo-tetrazol-5-yl-4H- 1-benzopyran hydrochloride salt (26.7 g; 1 equivalent ratio; prepared according to the method disclosed in US Pat. No. 4,780,469) and triethylamine (TEA, 10.1 g, 1 equivalent ratio, Aldrich) dissolved in 80 ml dimethylacetamide (DMAC, Aldrich) was slowly added to the mixture solution, and thermally stirred for 5 hrs at 25C. The reaction mixture was mixed with 300 ml H2O and stirred for 1 hr at 250C. The solid material obtained by filtering the solid material produced was washed with 100 ml H2O. 200 ml 50% acetone aqueous solution was added to the solid material and then refluxed for 1 hr. After the reaction mixture was cooled to room temperature, filtered and air-dried, the mixture was kept to stand on air for 5 hrs, obtaining 47.0 g pranlukart hemihydrates (yield rate: 98%): melting point 231-233C (decomposition); 1H-NMR (DMSO-d6, 300 MHz) delta 1.9 (m, 4H), 2,7 (m, 2H), 4.0 (t, 2H), 7.0 (s, 2H), 7.1 (s, IH), 7.2-7.3 (m, 5H), 7.6 (t, IH), 7.9 (t, IH), 8.0 (m, 2H), 8.3 (t, IH), 10.0 (bs, IH).
	With oxalyl dichloride;N,N-dimethyl-formamide; at 20℃; for 2h;	To a suspension of <strong>[30131-16-9]4-(4-phenylbutoxy)benzoic acid</strong> (5.40 g) in methylene chloride (20 mL) were added oxalyl chloride (2.09 mL) and N,N-dimethylformamide (1 drop), and the resulting mixture was stirred for 2 hours at room temperature and then concentrated. To a suspension of the compound prepared in Example 3 (5.61 g) in methylene chloride (60 mL) were added pyridine (4.85 mL) and the previously prepared acid chloride in methylene chloride (20 mL), with ice cooling and the resulting mixture was stirred for 3 hours at room temperature. The reaction mixture was concentrated and the residue was diluted with ethyl acetate. The diluted solution was washed sequentially with water, 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from a mixed solvent of ethyl acetate (100 mL) and n-hexane (100 mL) to give the title compound (8.58 g) having the following physical data. TLC: Rf 0.54 (n-hexane : ethyl acetate = 2 : 1).

References: [1]Patent: US5659051,1997,A .
[2]Patent: WO2010/2075,2010,A1 .Location in patent: Page/Page column 17-18.
[3]Patent: EP1661892,2006,A1 .Location in patent: Page/Page column 91-92.

8
[ 30131-16-9 ]
4-(4-phenylbutyloxy)benzyl alcohol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	In tetrahydrofuran; diethyl ether; water;	18C 4-(4-Phenylbutoxy)benzyl alcohol A suspension of lithium aluminium hydride (309 mg, 7.62 mmol) in anhydrous tetrahydrofuran (65 ml) was added under inert atmosphere with a solution of <strong>[30131-16-9]4-(4-phenylbutoxy)benzoic acid</strong> (1.03 g, 3.81 mmol) in 20 ml of dry ethyl ether. The mixture was left under stirring at room temperature for 2 hours, after that was added slowly with a NaCl saturated solution in water (80 ml), the two phases were separated and the aqueous one was extracted with ethyl acetate (3*50 ml). The organic extracts were dried and the solvent was evaporated off to obtain a crude, which was digested with ethyl ether. The digestion extracts were evaporated under reduced pressure to obtain 556 mg of the title compound (57% yield). 1 H N.M.R. (300 MHz, CDCl3) delta ppm: 1.79 (m, 4H); 2.65 (t, 2H); 3.92 (t, 2H); 4.54 (s, 2H); 6.85 (d, 2H); 7.13-7.28 (sc, 7H).

References: [1]Patent: US5990142,1999,A .

9
[ 108807-05-2 ]
[ 30131-16-9 ]
[ 136450-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In toluene;	(3) In a reactor, toluene (160 g) and 3-amino-2-hydroxyacetophenone (hereinafter referred to as "AHA") sulfate (the molecular weight, 249.3. 42.3 g) were charged and heated to 40 C. At the same temperature, to this solution, the solution of 4-(4-phenyl-1-butoxy)benzoyl chloride in toluene (79.3 g) obtained in the above step (2) and an aqueous solution of sodium carbonate (1.6 equivalents to <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>) were dropwise added simultaneously over a period of one hour, followed by heating at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was neutralized with hydrochloric acid. An organic layer was washed with water and phase separated. Then, the organic layer was cooled to 0 C. and maintained at that temperature to crystallize the product to obtain 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone (66.8 g). Yield of the pure product, 97.3% (based on AHA sulfate).
	With sodium carbonate; In toluene;	(3) In a reactor, toluene (80 g) and AHA hydrochloride (the molecular weight, 187.6. 15.9 g) were charged and heated to 40 C. At the same temperature, to this solution, the solution of 4-(4-phenyl-1-butoxy)benzoyl chloride in toluene (41.1 g) obtained in the above step (2) and an aqueous solution of sodium carbonate (1.2 equivalents to <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>) were dropwise added simultaneously over a period of one hour, followed by heating at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was neutralized with hydrochloric acid. An organic layer was washed with water and phase separated. Then, the organic layer was cooled to 0 C. and maintained at that temperature to crystallize the product to obtain 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone (33.4 g). Yield of the pure product, 96.9% (based on AHA hydrochloride).
	With sodium carbonate; In toluene;	(3) In a reactor, toluene (80 g) and AHA sulfate (21.3 g) were charged and heated to 40 C. At the same temperature, to this solution, the solution of 4-(4-phenyl-1-butoxy)benzoyl chloride in toluene (40.7 g) obtained in the above step (2) and an aqueous solution of sodium carbonate (1.6 equivalents to <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>) were dropwise added simultaneously over a period of one hour, followed by heating at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was neutralized with hydrochloric acid. An organic layer was washed with water and phase separated. Then, the organic layer was cooled to 0 C. and maintained at that temperature to crystallize the product to obtain 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone (33.6 g). Yield of the pure product, 95.2% (based on <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>).

	With sodium carbonate; In toluene;	(3) In a reactor, toluene (80 g) and AHA hydrochloride (16.0 g) were charged and heated to 40 C. At the same temperature, to this solution, the solution of 4-(4-phenyl-1-butoxy)benzoyl chloride in toluene (41.4 g) obtained in the above step (2) and an aqueous solution of sodium carbonate (1.3 equivalents to <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>) were dropwise added simultaneously over a period of one hour, followed by heating at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was neutralized with hydrochloric acid. An organic layer was washed with water and phase separated. Then, the organic layer was cooled to 0 C. and maintained at that temperature to crystallize the product to obtain 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone (32.1 g). Yield of the pure product, 93.3% (based on AHA hydrochloride).
	With sodium carbonate; In toluene;	(3) In a reactor, toluene (162.0 g) and AHA sulfate (43.3 g) were charged and heated to 45 C. At the same temperature, to this solution, the solution of 4-(4-phenyl-1-butoxy)benzoyl chloride in toluene (146.5 g) obtained in the above step (2) and an aqueous solution of sodium carbonate (1.6 equivalents to <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>) were dropwise added simultaneously over a period of one hour, followed by heating at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was neutralized with hydrochloric acid. An organic layer was washed with water and separated. Then, the organic layer was cooled to 0 C. and maintained at that temperature to crystallize the product to obtain 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone (68.8 g). Yield of the pure product, 96.7% (from the step (2), based on <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>).

References: [1]Patent: US5675036,1997,A .
[2]Patent: US5675036,1997,A .
[3]Patent: US5675036,1997,A .
[4]Patent: US5675036,1997,A .
[5]Patent: US5675036,1997,A .

10
[ 79-37-8 ]
[ 30131-16-9 ]
[ 108807-05-2 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; N,N-dimethyl-formamide;	REFERENCE EXAMPLE 12 STR54 One drop of N,N-dimethylformamide was added to a solution of 1 g of <strong>[30131-16-9]p-(4-phenylbutoxy)benzoic acid</strong> in 5 ml of methylene chloride and 2 ml of oxalyl chloride was added to the mixture at -30 C. or lower. The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure to obtain crude p-(4-phenylbutoxy)benzoyl chloride.
	In dichloromethane; N,N-dimethyl-formamide;	REFERENCE EXAMPLE 27 STR97 One drop of N,N-dimethylformamide was added to a solution of 1.41 g of <strong>[30131-16-9]p-(4-phenylbutoxy)benzoic acid</strong> in 35 ml of methylene chloride and 1.5 ml of oxalyl chloride was further added to the mixture under ice cooling. The mixture was stirred for 30 minutes and at room temperature for an additional 1 hour. The reaction mixture was concentrated under reduced pressure to obtain crude p-(4-phenylbutoxy)benzoyl chloride.

References: [1]Patent: US4994479,1991,A .
[2]Patent: US4994479,1991,A .

11
sodium p-phenylbutoxybenzoate [ No CAS ]
[ 30131-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In methanol; water; N,N-dimethyl-formamide; toluene; at 70℃; for 0.25h;Product distribution / selectivity;	In a flask equipped with a stirrer were put 56.7 g of methyl 4-hydroxybenzoate, 53.8 g of potassium carbonate (anhydrous) and 108.1 g of N,N-dimethyl formamide, and the inside temperature was elevated to 110C. After 60 g of 4-phenyl-1-chlorobutane was added dropwise at the same temperature over 2 hours, the mixture was stirred at the same temperature for 12 hours to react. 138 g of toluene was added thereto, and it was cooled until the inside temperature became not more than 80C, to which 180 g of water was added. The inside temperature was adjusted to 65C, and the liquid phase separation was conducted at the same temperature to give an oil layer and an aqueous layer. The oil layer was washed with 240g of water, then 180 g of 1wt% aqueous sodium hydroxide solution, and further180 g of water to give 246.7 g of an oil layer containing methyl 4-(4-phenylbutoxy)benzoate. Content: 39.0% Yield: 96% (4-phenyl-l-chlorobutane basis) The oil layer contained 0.20% (area percentage) of methyl 4-methoxybenzoate. The oil layer containing 239 g of methyl 4-(4-phenylbutoxy)benzoate, 29.3 g of methanol and 77 g of 27% by weight aqueous sodium hydroxide solution were mixed and the inside temperature was elevated to 70 to 75C, and the mixture was stirred at the same time for 3 hours to hydrolyze it. The hydrolyzed liquid was carefully poured into a mixture of 216.9 g of 18% by weight sulfuric acid and 175 g of toluene so that the liquid temperature was kept at not more than 70C, and then the mixture was stirred for 15 minutes. After 45.5 g of 27% by weight aqueous sodium hydroxide solution was added thereto at an inside temperature of 65C to adjust the pH to 5.5, the liquid phase separation was conducted. To the obtained organic layer was added 175 g of 10 wt% aqueous sodium sulfate solution, and the liquid phase separation was conducted at an inside temperature of 65C and a pH of 5 to 7. The procedure of liquid phase separation using the aqueous sodium sulfate solution was further repeated twice to give an organic layer containing 4-(4-phenylbutoxy)benzoic acid. Yield: 99.6% (methyl (4-(4-phenylbutoxy)benzoate basis) The above-mentioned organic layer contained 4-methoxybenzoic acid as much as 0.03% (area percentage).; In a flask equipped with a stirrer were put35.3 g of 4-phenyl-1-chlorobutane, 33g of methyl 4-hydroxybenzoate, 31.4 g of potassium carbonate (anhydrous), 52.5 g of N,N-dimethyl formamide and52.5 g of toluene, then the inside temperature was elevated to 125 to 128C, and the mixture was stirred at the same temperature for 10 hours to react. 24.5 g of toluene was added thereto, and it was cooled until the inside temperature became not more than 80C, and water was added thereto. The inside temperature was adjusted to 65C, and the liquid separation was conducted at the same temperature to give an oil layer and an aqueous layer. The oil layer was washed with 140g of water, then 105 g of a 1 wt% aqueous sodium hydroxide solution, and further 105 g of water to give 138 g of an oil layer containing methyl 4-(4-phenylbutoxy)benzoate. Content: 40.5% Yield: 96% (4-phenyl-l-chlorobutane basis) The oil layer contained 0.46% (area percentage) of methyl 4-methoxybenzoate. The oil layer containing 40 g of methyl 4-(4-phenylbutoxy)benzoate, 5.1 g of methanol and 13.6 g of 27 wt% aqueous sodium hydroxide solution were mixed and the inside temperature was elevated to 70 to 75C, and the mixture was stirred at the same time for 3 hours to hydrolyze it. The hydrolyzed solution was carefully poured into a mixture of 34.5 g of 10 wt% sulfuric acid and 31 g of toluene so that the liquid temperature was kept at not more than 70C, and then the mixture was stirred for 15 minutes. After 3.9 g of 20 wt% sulfuric acid was added thereto at an inside temperature of 65C to adjust the pH to 6.5, the liquid separation was conducted. To the obtained organic layer was added 31 g of 10 wt% aqueous sodium sulfate solution, and the liquid phase separation was conducted at an inside temperature of 65C and at a pH of 6 to 7. 31 g of 10% by weight aqueous sodium sulfate solution was added thereto, and the liquid separation was conducted once more at an inside temperature of 65C and at a pH of 6 to 7. 31 g of water was added to the obtained organic layer and the liquid separation was conducted at an inside temperature of 65C and a pH of 6 to 7 to give an organic layer containing 4-(4-phenylbutoxy)benzoic acid. Yield: 98.9% (methyl 4-(4-phenylbutoxy)benzoate basis) The above-mentioned organic layer contained 4-methoxybenzoic acid in a content of not more than 0.01% (area percentage).; In a flask equipped with a stirrer were put 33 g of methyl 4-hydroxybenzoate, 31.4 g of potassium carbonate (anhydrous) and 51.5 g of N,N-dimethyl formamide, and the inside temperature was elevated to 100C. After 35 g of 4-phenyl-1-chlorobutane was added dropwise thereto at the same temperature over 2 hours, the mixture was stirred at the same temperature for 7 hours to react....

References: [1]Patent: EP1739071,2007,A1 .Location in patent: Page/Page column 7-8.

12
[ 3360-41-6 ]
[ 30131-16-9 ]

References: [1]Patent: CN103588638,2016,B .
[2]Patent: CN103588638,2016,B .
[3]Patent: CN103588638,2016,B .

13
[ 623-03-0 ]
[ 30131-16-9 ]

References: [1]Patent: CN103588638,2016,B .
[2]Patent: CN103588638,2016,B .
[3]Patent: CN103588638,2016,B .

14
[ 138631-41-1 ]
[ 30131-16-9 ]

Yield	Reaction Conditions	Operation in experiment
98.2%	With sulfuric acid; In water; at 120℃; for 5h;	((1) thermal reaction: the four port in the clean and dry in the reaction bottle, filled with stirring and reflux condenser, to reaction bottle 151g phenyltheophylline butanol (content is 99.0%, 1mol), then with according to benzene CH 3 ONa amount-of-substance ratio 1 : 0.4 adding CH 3 ONa (CH 3 ONa for folds hundred quantities 21.6g), wherein CH 3 ONa configured to first the mass fraction of 30% with fresh methanol solution, the temperature is increased to 130 C, reaction 2h after cooling to 100 C; (2) condensation reaction: to the above-mentioned under the protection of nitrogen added in the reaction solution after temperature 55.6g (content of 99%, 0 . 4mol) 4-chlorophenyl nitrile, heating to 100 C reaction 15h, cooling to room temperature, the toluene and water added to 200 ml, stirring 30 min to mix, and then layering, with water 200 ml toluene a re-extraction, extraction combined toluene layer, pressure-reducing recovery toluene and excessive benzene butylacohol , shown in formula (IV) is 4-( benzene butoxy) benzoate object nitrile oil 103.8g, the purity of 95.0% (GC), molar yield of 98.1% (to 4-chlorobenzene nitrile idea); (3) direct hydrolysis reaction: the above-mentioned is obtained by reacting 4-( benzene butoxy) nitrile oil -benzoate (103.8g, the purity of 95.0%, 0 . 39mol) into 200 ml water, with a 98% concentrated sulfuric acid of pH of the aqueous 1, the temperature rising to 120 C hydrolysis reaction 5h after cooling to room temperature, precipitating a large amount of white solid, filtering, the water washing of the filter cake to neutral pH, hot air drying, to obtain the formula (I) indicated by 4-( benzene butoxy) benzoic acid white crystal 104.6g, melting point 130-131C, molar yield 98.2% (4-( benzene butoxy) benzonitrile nitrile idea), purity 99.6% (HPLC).

References: [1]Patent: CN103588638,2016,B .Location in patent: Paragraph 0041-0045.
[2]Patent: CN103588638,2016,B .

15
ethyl 4-(phenylbutoxy)benzoate [ No CAS ]
[ 30131-16-9 ]

Yield	Reaction Conditions	Operation in experiment
98.6%	With sulfuric acid; In water; at 100℃; for 1h;	A 4-( benzene butoxy) benzoic acid synthesis method, the method for synthesizing carried out according to the following steps: (1) thermal reaction: the alkali to C 2 H 5 ONa, with according to benzene C 2 H 5 ONa amount-of-substance ratio 1 : 0.4 adding C 2 H 5 ONa (C 2 H 5 ONa for folds hundred quantities 27.2g), wherein C 2 H 5 ONa to dispose into the mass fraction is 30% of the fresh ethanol solution and then use, other operation with the embodiment 1; (2) condensation reaction: with the embodiment 1, as shown in formula (IV) of the obtained 4-( benzene butoxy) benzoate object nitrile oil 103.7g, the purity of 95.3% (GC), the molar yield 98.3% (to 4-chlorobenzene nitrile idea); (3) alcoholysis reaction: the above-mentioned is obtained by reacting 4-( benzene butoxy) nitrile oil -benzoate (103.7g, the purity of 95.3%, 0 . 393mol) adding 518.5g in anhydrous ethanol, heating in the 60 C alcoholysis reaction under 8h after cooling to room temperature, recycling excess of ethanol, then adding toluene and water all 200 ml, stirring 30 min to mix, and then layering, with water 200 ml toluene a re-extraction, extraction combined toluene layer, pressure-reducing recovery toluene, to obtain the formula (V) as shown in 4-( benzene butoxy) benzoic acid ethyl ester oil objects 117.8g, the purity is 98.1% (GC), molar yield of 98.5% (to 4-( benzene butoxy) benzonitrile nitrile idea); (4) the hydrolysis reaction of the alcoholysis after: the above-mentioned reaction of the 4-( benzene butoxy) benzoic acid ethyl ester oil objects (117.8g, the purity is 98.1%, 0 . 387mol) into 200 ml water, with a 98% concentrated sulfuric acid for adjusting the pH of the aqueous solution 2, the temperature is increased to 100 C hydrolysis reaction 1h after cooling to room temperature, precipitating a large amount of white solid, filtering, the water washing of the filter cake to neutral pH, hot air drying, to obtain the formula (I) indicated by 4-( benzene butoxy) benzoic acid white crystal 79.3g, melting point 130-131C, molar yield 98.6% (4-( benzene butoxy) benzonitrile nitrile idea), purity 99.8% (HPLC).

References: [1]Patent: CN103588638,2016,B .Location in patent: Paragraph 0056-0060.

16
[ 30131-16-9 ]
[ 70977-72-9 ]
[ 136450-06-1 ]

Yield	Reaction Conditions	Operation in experiment
84%		270 g of 4- (phenylbutoxy) benzoic acid was added, 270 g of thionyl chloride was added and incubated at 50 C for 3 hours. After completion of the reaction, the unreacted thionyl chloride was recovered under reduced pressure. Nitrogen blowing into the thiophene chloride. Cooled to room temperature by adding 270 g of dichloromethane. Weigh 151 g of 3-amino-2-hydroxyacetophenone in 200 g of methylene chloride, 160 g of pyridine was added, and a solution of 4- (phenylbutoxy) benzoyl chloride in methylene chloride was added dropwise to the ice bath. The temperature is not more than 10 , dripping finished, 10 incubation reaction 2h, after the end of the reaction, adding to the reaction system dilute hydrochloric acid, adjust the pH to 2-3, liquid, methyl chloride layer washed to neutral, anhydrous Dried over sodium sulfate, filtered and concentrated to give a reddish brown solid, petroleum ether: ethyl acetate = 1: 1 recrystallization to give 334 g, yield 84%.

References: [1]Patent: CN106588897,2017,A .Location in patent: Paragraph 0019.

17
[ 30131-16-9 ]
2-[4-(4-phenylbutoxy)benzoylamino]-6-(1,3-dicarbonyl-3-tetrazolyl)phenol [ No CAS ]

References: [1]Patent: CN106588897,2017,A .

18
[ 30131-16-9 ]
[ 103177-37-3 ]

References: [1]Patent: CN106588897,2017,A .

19
[ 30131-16-9 ]
4-[4-(4-phenylbutyloxy)benzoyloxy]benzoic acid [ No CAS ]

References: [1]New Journal of Chemistry,2017,vol. 41,p. 4672 - 4679.

20
[ 30131-16-9 ]
7-{4-[4-(4-phenylbutyloxy)]benzoyloxy}benzoyloxynaphthalen-2-yl 4-(4-dodecyloxybenzoyloxy)benzoate [ No CAS ]

References: [1]New Journal of Chemistry,2017,vol. 41,p. 4672 - 4679.

21
[ 30131-16-9 ]
[ 123-08-0 ]
4-formylphenyl 4-(4-phenylbutyloxy)benzoate [ No CAS ]

References: [1]New Journal of Chemistry,2017,vol. 41,p. 4672 - 4679.

22
[ 13633-25-5 ]
[ 30131-16-9 ]

References: [1]New Journal of Chemistry,2017,vol. 41,p. 4672 - 4679.
[2]ChemMedChem,2018,vol. 13,p. 2530 - 2545.

23
[ 1589-82-8 ]
[ 30131-16-9 ]

References: [1]New Journal of Chemistry,2017,vol. 41,p. 4672 - 4679.

24
[ 4830-93-7 ]
[ 99-96-7 ]
[ 30131-16-9 ]

Yield	Reaction Conditions	Operation in experiment
85.2%	With potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; at 130 - 140℃; for 24h;Inert atmosphere;	Into a 500 ml four-necked flask, nitrogen was added for protection, and 75 g of 1-chloro-4-phenylbutane, 69 g of p-hydroxybenzoic acid, 65 g of potassium carbonate, 175 g of xylene, and 0.75 g of polyethylene glycol were added. After refluxing at 130~140 C for 24h, after high-performance liquid chromatography (HPLC), the temperature is lowered to room temperature, 1~5% liquid alkali is added for washing, xylene is concentrated, methanol is added to dissolve, and the reaction temperature is adjusted to be less than At 20 C, filtration, partial concentration of methanol, and filtration under reduced temperature gave p-butoxybenzoic acid with a molar yield of 85.2% and a purity of 98.56% (detected by high performance liquid chromatography (HPLC)). The synthesis process in the embodiment is simple in steps and convenient in operation, and avoids the production of the highly toxic intermediate phenylbutane bromide and a large amount of waste water in the synthesis process, so that the environment is friendly and the production cost is saved, and the pair obtained by the process is synthesized. Phenylbutoxybenzoic acid has high purity and is suitable for large-scale industrial production

References: [1]Patent: CN108558916,2018,A .Location in patent: Paragraph 0052; 0079; 0082; 0083; 0086.

25
[ 13633-25-5 ]
[ 99-76-3 ]
[ 30131-16-9 ]

Yield	Reaction Conditions	Operation in experiment
98.7%		Step 1. In a 250 ml three-necked flask, 1 g of a catalyst P-W2CNC, 1-bromo-4-phenylbutane 8.0 g, DMF 50 ml, and mechanical stirring were sequentially added.Put 1.8 g of methylparaben, K2CO 33.6 g, and heat to 115 C.Reaction 11h;Step 2: After the reaction is cooled to room temperature, the K2CO3 solid is removed by suction filtration.Add 50 ml of water to the filtrate, turbid, stir for 10 min, add about 3 mol / L of HCl solution to adjust pH = 2;Step 3. Extract the above system with dichloromethane, wash with ionized water,The solvent dichloromethane was removed by rotary evaporation to give an orange liquid;Step 4, the orange liquid is placed in a single-mouth bottle, 3.0 g of NaOH, 50 ml of water and 40 ml of ethanol are added, and the mixture is refluxed for 3 hours in an oil bath, and the ethanol is distilled off.The residue was adjusted to pH=2 with 3 mol/L of HCl;Step 5, after extracting the above system with dichloromethane, the organic phase is steamed.A sticky yellow solid was obtained, and after adding an appropriate amount of isopropanol, the mixture was stirred, solid crystallized, and suction filtered to give white crystals of 4-(4-phenylbutoxy)benzoic acid.

References: [1]Patent: CN108689843,2018,A .Location in patent: Paragraph 0010-0031.

26
[ 30131-16-9 ]
[ 103195-35-3 ]
4-oxo-8-(4-(4-phenylbutoxy)benzamido)chromene-2-carboxylic acid [ No CAS ]