4521-22-6|4-(p-Tolyl)butanoic acid| Ambeed

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Quality Control of [ 4521-22-6 ] Purity: 97% SDS Specification

COA

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NMR

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CNMR

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Product Details of [ 4521-22-6 ]

CAS No. :	4521-22-6
Formula :	C₁₁H₁₄O₂
M.W :	178.23
SMILES Code :	O=C(O)CCCC1=CC=C(C)C=C1
MDL No. :	MFCD00021786
Boiling Point :	No data available
InChI Key :	IXWOVMRDYFFXGI-UHFFFAOYSA-N
Pubchem ID :	78279

Safety of [ 4521-22-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 4521-22-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.36
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	52.57
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.87
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	2.78
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.4
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.	2.58
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	2.73
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.47

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.77
Solubility	0.3 mg/ml ; 0.00168 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.22
Solubility	0.108 mg/ml ; 0.000604 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.37
Solubility	0.076 mg/ml ; 0.000427 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	No
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	No
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	No
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.	-5.41 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	1.0
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)	1.08

Application In Synthesis of [ 4521-22-6 ]

* 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 [ 4521-22-6 ]

[ 4521-22-6 ] Synthesis Path-Downstream 1~35

1
[ 96-48-0 ]
[ 108-88-3 ]
[ 4521-22-6 ]

References: [1]Monatshefte fur Chemie,1957,vol. 88,p. 517,527.

2
[ 1079-72-7 ]
[ 4521-22-6 ]

References: [1]Chemische Berichte,1959,vol. 92,p. 916,918.

3
[ 4160-52-5 ]
[ 4521-23-7 ]
[ 4521-22-6 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1910,vol. <2> 81,p. 74.

4
[ 41010-07-5 ]
[ 4521-22-6 ]

References: [1]Annales de Chimie (Cachan, France),1959,vol. <13> 4,p. 43,53.

5
[ 4619-20-9 ]
2,2'-di-p-tolyl-tetrahydro-[2,2']bifuryl-5,5'-dione [ No CAS ]
[ 4521-22-6 ]

References: [1]Journal of the Chinese Chemical Society,1943,vol. 10,p. 119,122.

6
[ 4619-20-9 ]
[ 4521-22-6 ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1991,vol. 57,p. 227 - 233.
[2]Australian Journal of Chemistry,1990,vol. 43,p. 1547 - 1557.
[3]Tetrahedron,1985,vol. 41,p. 1509 - 1516.
[4]Journal of the Chemical Society,1956,p. 3857,3860.
[5]Journal of the American Chemical Society,1936,vol. 58,p. 572,575.
[6]Journal of the American Chemical Society,1949,vol. 71,p. 1036.
[7]Bulletin of the Chemical Society of Japan,1979,vol. 52,p. 3033 - 3042.
[8]Journal of Organic Chemistry,1962,vol. 27,p. 857 - 863.
[9]European Journal of Medicinal Chemistry,1996,vol. 31,p. 683 - 692.
[10]Synthetic Communications,2001,vol. 31,p. 1467 - 1475.
[11]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5586 - 5590.
[12]ARKIVOC,2010,vol. 2010,p. 40 - 53.
[13]Journal of Molecular Structure,2010,vol. 980,p. 59 - 65.
[14]Angewandte Chemie - International Edition,2016,vol. 55,p. 15797 - 15801.
Angew. Chem.,2016,vol. 128,p. 16029 - 16033,5.
[15]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2894 - 2899.
[16]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 1672 - 1683.
[17]Chemical Communications,2019,vol. 55,p. 933 - 936.
[18]Angewandte Chemie - International Edition,2019,vol. 58,p. 16490 - 16494.
Angew. Chem.,2019,vol. 131,p. 16642 - 16646,5.

7
[ 4619-20-9 ]
[ 36440-63-8 ]
[ 4521-22-6 ]

References: [1]Chemische Berichte,1919,vol. 52,p. 2079.

8
[ 54540-53-3 ]
[ 4521-22-6 ]

References: [1]Annales de Chimie (Cachan, France),1959,vol. <13> 4,p. 43,53.
[2]Annales de Chimie (Cachan, France),1959,vol. <13> 4,p. 43,53.

9
[ 122-39-4 ]
[ 4521-22-6 ]
9-(3-p-tolyl-propyl)-acridine [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1945,vol. 64,p. 250,253.

10
[ 4521-22-6 ]
[ 22009-37-6 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 4007 - 4010.
[2]Chemistry Letters,2008,vol. 37,p. 320 - 321.
[3]Australian Journal of Chemistry,1990,vol. 43,p. 1547 - 1557.
[4]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2894 - 2899.
[5]Chemische Berichte,1923,vol. 56,p. 630.
[6]Chemische Berichte,1923,vol. 56,p. 1431.
[7]Journal of the Chemical Society,1954,p. 798.
[8]Journal of the Chemical Society,1933,p. 434,436.
[9]Bulletin de la Societe Chimique de France,1970,p. 146 - 150.
[10]Journal of the American Chemical Society,1974,vol. 96,p. 5130 - 5138.
[11]Journal of Organic Chemistry,1962,vol. 27,p. 857 - 863.
[12]Journal of Medicinal Chemistry,1977,vol. 20,p. 1059 - 1064.
[13]Helvetica Chimica Acta,1932,vol. 15,p. 907,914.
[14]ARKIVOC,2010,vol. 2010,p. 40 - 53.
[15]Journal of Molecular Structure,2010,vol. 980,p. 59 - 65.
[16]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 1672 - 1683.

11
[ 4521-22-6 ]
[ 1680-51-9 ]

References: [1]Journal of the Indian Chemical Society,1948,vol. 25,p. 323,327.
[2]Australian Journal of Chemistry,1990,vol. 43,p. 1547 - 1557.
[3]Journal of the Chemical Society,1961,p. 4794 - 4808.

12
[ 4521-22-6 ]
4-(4-methyl-cyclohexyl)-butyric acid [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3177.
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5043 - 5047.

13
[ 4521-22-6 ]
[ 160699-02-5 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; N,N-dimethyl-formamide; In benzene; at 80℃; for 2h;	(1a) (2R)-1-Acetoxy-2-acetylamino-2-methyl-4-{1-methyl-5-[4-(4-methylphenyl)-1-(4-(4-methylphenyl)butanoyloxy)but-1-enyl]pyrrol-2-yl}butane Thionyl chloride (9.0 mL, 123 mmol) and N,N-dimethylformamide (50 muL) were added to a solution of <strong>[4521-22-6]4-(4-methylphenyl)butyric acid</strong> (11.0 g, 62.0 mmol) in benzene (220 mL) and the mixture was stirred at 80C for 2 hours. After cooling the mixture to room temperature, the solvent was evaporated under reduced pressure to obtain 5-(4-methylphenyl)butyric chloride. A solution of 4-dimethylaminopyridine (15.2 g, 124 mmol) and 4-(4-methylphenyl)butyric chloride (12.2 g, 62.0 mmol) in toluene (50 mL) was added to a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-(1-methylpyrrol-2-yl)butane (5.00 g, 18.8 mmol) obtained in Reference example 1 in toluene (150 mL) and the mixture was stirred at 110C for 48 hours. The temperature of the mixture was returned to room temperature and ethyl acetate and water were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with water and a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane, 3:2-2:1) to obtain the title compound (5.15 g, yield: 47%).
	With oxalyl dichloride; In methyl cyclohexane; N,N-dimethyl-formamide; at 20℃; for 2h;Inert atmosphere;	4-(4-Methylphenyl)butyryl chloride (20.8 g) was dissolved in MCH (95 mL), and to the resulting solution, DMF (90 muL) and oxalyl chloride (15.9 g) were added at room temperature under a nitrogen atmosphere. After stirring the resulting solution at that temperature for 2 hours, the MCH was distilled off at a degree of reduced pressure of 2.7 to 7.5 kPa and an external temperature of 60C (an internal temperature of approximately 50 to 60C). MCH (36 mL) was added thereto again and was distilled off at a degree of reduced pressure of 2.7 to 7.5 kPa and an external temperature of 60C (an internal temperature of approximately 50 to 60C). The thus prepared 4-(4-methylphenyl)butyryl chloride solution was allowed to stand overnight under a nitrogen atmosphere, and then was used for acylation (1-2) without purification.
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0℃; for 0.25h;	In a 25 mL flask, 3-(p-tolylthio)propanoic acid (0.95 g, 5.43 mmol) was dissolved in dry DCM (17 mL) under argon atmosphere. Oxalyl chloride (0.46 mL, 5.43 mmol) and DMF (0.03 mL) were successively added to the reaction mixture at 0C. After 15 minutes of stirring, the apparition of bubbles stopped. Oxalyl chloride and DCM were evaporated under vacuum. To a solution of this resulting 42 3-(p-tolylthio)propanoyl chloride in dry 8 DCM (1.5 mL) were added dropwise at 0C 33 4-amino-N-(2,5-dimethoxyphenyl) benzenesulfonamide (0.56 g, 1.81 mmol) dissolved in 12 mL of dry DCM and 49 Et3N (0.36 mL, 2.7 mmol). After stirring at room temperature over 24 hours, the reaction mixture was quenched with 5% 43 sodium bicarbonate solution. The aqueous layer was extracted three times with DCM. The combined organic layers were washed successively with a molar solution of 44 HCl, and then with brine. After drying over MgSO4 and removal under vacuum of the solvent, the crude was purified by chromatography over silica gel (PE/EtOAc : 8/2 to 1/1) affording the expected 68 compound (3) as a white solid (0.250 g, 0.533 mmol) with 30 % yield. (Rf: 0.62 (DCM/EtOAc: 9/1); mp: 126 C). RMN 1H (300 MHz, CDCl3): 7.70 (d, 2H, H11-H12), 7.68 (d, 2H, H10-H13), 7.45 (s, 1H, H15), 7.13 (m, 5H, H2-5-H15), 6.64 (d, 1H, H17), 6.52 (dd, 1H, H16), 3.73 (s, 3H, CH3), 3.61 (s, 3H, CH3), 2.63 (t, 2H, H8), 2.32 (m, 5H, H1-H6), 2.01 (q, 2H, H7). RMN 13C (75 MHz, CDCl3): 171.5 (CO), 153.8 (CO), 143.5 (CO), 142.2 (CIV), 138.0 (CIV), 135.6 (CIV), 133.6 (CIV), 129.2 - 128.6 (C2-5), 128.4 (C11-C12) 126.5 (CIV), 118.9 (C10-C13), 111.5 (C17), 109.7 (C16), 107.1 (C15), 56.2 (CH3), 55.8 (CH3), 36.7 (C7), 34.5 (C8), 31.0 (C6), 26.7 (C7), 21.0 (C1). HRMS: Calculated for [M+Na]+: 491.1617; Measured: 491.1617 IR: 3316 (v N-H), 3267 (v N-H), 3025 (v Car-H), 2943 (v Cal-H), 2841 (v OC-H), 1663 (v C=O), 1338 (vas SO2), 1312 (Amide III), 1157 (vs SO2)

References: [1]Helvetica Chimica Acta,1932,vol. 15,p. 907,914.
[2]Organic and Biomolecular Chemistry,2009,vol. 7,p. 167 - 177.
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 7625 - 7634.
[4]Patent: EP1733724,2006,A1 .Location in patent: Page/Page column 38.
[5]Patent: EP2647635,2013,A1 .Location in patent: Paragraph 0044; 0045.
[6]Patent: EP3412652,2018,A1 .Location in patent: Paragraph 0094-0096.
[7]Journal of the American Chemical Society,2019.
[8]Journal of the American Chemical Society,2019,vol. 141,p. 19048 - 19057.

14
[ 186581-53-3 ]
[ 4521-22-6 ]
[ 24306-23-8 ]

References: [1]Journal of the Chemical Society B: Physical Organic,1969,p. 439 - 445.

15
[ 64-17-5 ]
[ 4521-22-6 ]
[ 36440-63-8 ]

References: [1]Bulletin of the Chemical Society of Japan,1979,vol. 52,p. 3033 - 3042.
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 16490 - 16494.
Angew. Chem.,2019,vol. 131,p. 16642 - 16646,5.

16
[ 3282-30-2 ]
[ 4521-22-6 ]
C₁₆H₂₂O₃ [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1583 - 1588.

17
[ 67-56-1 ]
[ 4521-22-6 ]
[ 24306-23-8 ]

Yield	Reaction Conditions	Operation in experiment
59.1 g	With sulfuric acid; at 20℃; for 16h;	A mixture of <strong>[4521-22-6]4-(4-methylphenyl)butanoic acid</strong> (50 g, 260 mmol, 1.0 eq.), MeOH (300 ml_), and sulfuric acid (5 ml_) was stirred at room temperature for 16 h, then concentrated under reduced pressure. The residue was quenched by the addition of sat. NaHC03 (200 ml_) and the aqueous mixture was extracted with EtOAc (2 c 200 ml_). The combined organic layers were washed with brine, dried (Na2S04), and concentrated to give 59.1 g of methyl 4-(4-methylphenyl)butanoate as yellow oil.

References: [1]Tetrahedron,1985,vol. 41,p. 1509 - 1516.
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 15797 - 15801.
Angew. Chem.,2016,vol. 128,p. 16029 - 16033,5.
[3]Journal of the American Chemical Society,2019,vol. 141,p. 7797 - 7806.
[4]Patent: WO2019/169270,2019,A1 .Location in patent: Paragraph 0111.

18
[ 4521-22-6 ]
[ 21034-27-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	With ammonium iodide; Oxone; potassium bromide; In 2,2,2-trifluoroethanol; acetonitrile; at 20℃; for 12h;Green chemistry;	General procedure: To a mixture of MeCN and CF3CH2OH (6:4) (5.0 mL), carboxylic acid 1 (0.5 mmol), NH4I (0.25mmol), KBr (0.4 mmol) and Oxone? (0.75 mmol) were added. The resulting solution was stirred at room temperature for 12 h and then solvents were removed under reduced pressure. Water (10mL), sat. aq Na2S2O3 (4 mL) and sat. aq Na2CO3 (4 mL) were added to the residue and the mixture was stirred for another 5 min. The mixture was extracted with CH2Cl2 (3×10 mL) and the combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative TLC on silica gelusing (hexane-AcOEt 3:1) as eluant to give the pure product of aryl lactone 2.

References: [1]Chemical Communications,2019,vol. 55,p. 933 - 936.
[2]Helvetica Chimica Acta,2014,vol. 97,p. 854 - 860.
[3]Synthetic Communications,2014,vol. 44,p. 1608 - 1613.
[4]Synthetic Communications,2001,vol. 31,p. 1467 - 1475.
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1202 - 1203.

19
[ 4521-22-6 ]
[ 53392-07-7 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of 4-(4-Methylphenyl) butanol To lithium aluminum hydride (427 mg, 11.2 mmol) suspended in dry ether (5 ml) at 0 C. is added 1 g of 4-(4-methylphenyl) butanoic acid (5.614 mmol) dissolved in dry ether (10 ml) over a period of 30 minutes. The reaction mixture is then warmed to room temperature and stirred for 4 hours. Water (0.43 ml), NaOH (15% solution, 0.43 g) and water (1.29 ml) are then added successively and the resulting solution is stirred for 30 minutes. The precipitate is filtered and washed with ether and dried. This is then concentrated and purified by flash chromatography (silica gel; ethyl acetate/hexanes) as the eluding medium.
		Synthesis of 4-(4-Methylphenyl) butanol To lithium aluminum hydride (427 mg, 11.2 mmol) suspended in dry ether (5 ml) at 0 C. is added 1 g of 4-(4-methylphenyl) butanoic acid (5.614 mmol) dissolved in dry ether (10 ml) over a period of 30 minutes. The reaction mixture is then allowed to warm to room temperature and stirred for 4 hours. Water (0.43 ml), NaOH (15% solution, 0.43 g) and water (1.29 ml) were then added successively and the resulting solution is stirred for 30 minutes. The resulting precipitate is filtered and washed with ether and dried.
	With lithium aluminium tetrahydride; In diethyl ether; at 20℃; for 4h;	To lithium aluminum hydride (427 mg, 11.2 mmol) suspended in dry ether (5 ml) at 0 C. is added 1 g of 4-(4- methylphenyl)butanoic acid (5.614 mmol) dissolved in dry ether (10 ml) over a period of 30 minutes. The reaction mixture is then allowed to warm to room temperature and stirred for 4 hours. Water (0.43 ml), NaOH (15% solution, 0.43 g)and water (1.29 ml) were then added successively and theresulting solution is stirred for 30 minutes. The resultingprecipitate is filtered and washed with ether and dried. The filtrate is then concentrated and purified by flash chromatography using ethyl acetate-hexanes as the eluting medium.

References: [1]Journal of the American Chemical Society,1974,vol. 96,p. 5130 - 5138.
[2]European Journal of Medicinal Chemistry,1996,vol. 31,p. 683 - 692.
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5586 - 5590.
[4]Patent: US2005/191238,2005,A1 .Location in patent: Page/Page column 51.
[5]Patent: US2005/191238,2005,A1 .Location in patent: Page/Page column 57.
[6]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272.
[7]Patent: US9408927,2016,B2 .Location in patent: Page/Page column 67; 68.

20
[ 188290-36-0 ]
[ 4521-22-6 ]
1-Thiophen-2-yl-4-p-tolyl-butan-1-one [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,1998,vol. 48,p. 840 - 849.

21
[ 4521-22-6 ]
[ 104426-51-9 ]
3,3-Dimethyl-5-[5-(4-p-tolyl-butyryl)-thiophen-2-yl]-pentanoic acid methyl ester [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,1998,vol. 48,p. 840 - 849.

23
[ 7664-93-9 ]
[ 4521-22-6 ]
[ 22009-37-6 ]

References: [1]Chemische Berichte,1923,vol. 56,p. 630.

24
[ 7719-09-7 ]
[ 4521-22-6 ]
petroleum ether [ No CAS ]
[ 22009-37-6 ]

References: [1]Chemische Berichte,1923,vol. 56,p. 1431.

Yield	Reaction Conditions	Operation in experiment
		A. 4-(4-Methylphenyl)butyric acid To a 2 liter round-bottomed flask equipped with condenser and drying tube were added 68 grams (0.68 mol) succinic anhydride, 478 ml dry toluene, and 140 grams (1.05 mol) aluminum chloride in three portions (allowing the brisk hydrochloric acid evolution to subside after each portion). The reaction was heated until evolution of hydrogen chloride gas ceased, and then was cooled and quenched by dropwise addition of 200 mL water. Swirling was continued as 100 mL concentrated hydrochloric acid was added. The resulting solid was filtered, washed with 1N hydrochloric acid, water, and hexane three times, and then dried to a white solid (M.P. 122-126 C.) which still contained aluminum salts and water, but was suitable for the following step. To a 2L round-bottomed flask equipped with condenser were added 240 grams mossy zinc, 24 grams mercuric chloride, 400 mL water, and 11 mL concentrated hydrochloric acid. After swirling for 5 minutes, the aqueous layer was decanted, and the solid washed with a little water. To the residue were added 150 mL water, 350 mL concentrated hydrochloric acid (causing an exotherm and gas evolution), 200 mL toluene, and the above solid. The mixture was heated to reflux, and 50 mL concentrated hydrochloric acid was added after each of 5, 7, 9, and 22 hours. After 25 hours at reflux, the reaction was cooled, the layers separated, and the aqueous layer washed with ether. The combined organic layers were washed with water and brine, dried over sodium sulfate, and evaporated to give a solid, 103 grams (85% for 2 steps). 1 H NMR (delta, CDCl3): 2.00 (m, 2H), 2.37 (s, 3H), 2.42 (t, J=7, 2H), 2.69 (t, J=7, 2H), 7.14 (m, 4H).

26
[ 1143-38-0 ]
[ 4521-22-6 ]
1,8-dihydroxy-10-(4-p-tolyl-butyryl)-10H-anthracen-9-one [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 179 - 184.

27
[ 4521-22-6 ]
[ 294862-31-0 ]
[ 294862-40-1 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3730 - 3743.

28
[ 108-88-3 ]
poly[styrene (iodoso diacetate)] [ No CAS ]
[ 4521-22-6 ]

References: [1]Synthetic Communications,2001,vol. 31,p. 1467 - 1475.

29
[ 4521-22-6 ]
[ 182809-13-8 ]

References: [1]Arzneimittel-Forschung/Drug Research,1998,vol. 48,p. 840 - 849.

30
[ 4521-22-6 ]
5-[5-(4-p-Tolyl-butyl)-thiophen-2-yl]-pentanoic acid [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,1998,vol. 48,p. 840 - 849.

31
[ 4521-22-6 ]
3-Methyl-5-[5-(4-p-tolyl-butyl)-thiophen-2-yl]-pentanoic acid [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,1998,vol. 48,p. 840 - 849.

32
[ 4521-22-6 ]
[ 182809-11-6 ]

References: [1]Arzneimittel-Forschung/Drug Research,1998,vol. 48,p. 840 - 849.

33
[ 4521-22-6 ]
[ 214618-28-7 ]

References: [1]Arzneimittel-Forschung/Drug Research,1998,vol. 48,p. 840 - 849.

34
[ 4521-22-6 ]
5-Oxo-5-[5-(4-p-tolyl-butyl)-thiophen-2-yl]-pentanoic acid [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,1998,vol. 48,p. 840 - 849.

35
[ 4521-22-6 ]
[ 182809-10-5 ]

References: [1]Arzneimittel-Forschung/Drug Research,1998,vol. 48,p. 840 - 849.

Historical Records

Technical Information

• Arndt-Eistert Homologation • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • Hunsdiecker-Borodin Reaction • Hydrogenolysis of Benzyl Ether • Passerini Reaction • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction • Vilsmeier-Haack Reaction

Related Functional Groups of
[ 4521-22-6 ]

Aryls

A148817 [1821-12-1]

4-Phenylbutanoic acid

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A219211 [22084-89-5]

3-(2-Methylphenyl)propionic acid

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A368010 [5467-53-8]

4-(4-Ethylphenyl)butanoic acid

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A839937 [3751-48-2]

3-(3-Methylphenyl)propionic acid

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A414852 [42287-87-6]

3-(3,5-Dimethylphenyl)propanoic acid

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Carboxylic Acids

A148817 [1821-12-1]

4-Phenylbutanoic acid

Similarity: 1.00

A219211 [22084-89-5]

3-(2-Methylphenyl)propionic acid

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A368010 [5467-53-8]

4-(4-Ethylphenyl)butanoic acid

Similarity: 1.00

A839937 [3751-48-2]

3-(3-Methylphenyl)propionic acid

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A414852 [42287-87-6]

3-(3,5-Dimethylphenyl)propanoic acid

Similarity: 1.00

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CAS No.: 4521-22-6

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