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Chemical Structure| 119-61-9 Chemical Structure| 119-61-9
Chemical Structure| 119-61-9

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Benzophenone is an endogenous metabolite.

Synonyms: Diphenyl ketone; Benzoylbenzene; Diphenylmethanone

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Wackerly, Jay Wm ; Dunne, James F ; Shriver, James A ;

Abstract: A straightforward synthesis of diphenhydramine, a common medication known to most undergraduate students, is described for implementation as a capstone into the first-semester organic chemistry laboratory curriculum. This multistep synthesis converts benzophenone to the bromide salt of diphenhydramine using first-semester reactions including reduction and substitution. This rigorously developed procedure was undertaken independently by the three coauthors and verification was conducted externally to the home institution. Assessment of two major learning objectives indicates general success, but also points to places where students can improve. In developing this synthetic procedure, the concept of a modular approach was developed for an organic chemistry laboratory to allow application at a broad array of institutions; individualized adaptation of this procedure can fit a variety of learning objectives as needed. A detailed supplementary section is included to support instructors who may wish to implement elements of this procedure or the modules into their laboratory curriculum.

Keywords: Organic Chemistry I ; Multistep Synthesis ; Pre-Health ; Medicine ; Modular Laboratory ; Spectroscopy ; Substitution Reactions

Purchased from AmBeed: 67-68-5 ;

Christopher K. Webber ; Erica K. Richardson,Diane A. Dickie ; T. Brent Gunnoe ;

Abstract: Pyridine-alkoxide (pyalk) ligands that support transition metals have been studied for their use in electrocatalytic applications. Herein, we used the pyalk proligands diphenyl(pyridin-2-yl)methanol ([H]PhPyalk, L1), 1-(pyren-1-yl)-1-(pyridin-2-yl)ethan-1-ol ([H]PyrPyalk, L2), 1-(pyridine-2-yl)-1-(thiophen-2-yl)ethan-1-ol ([H]ThioPyalk, L3), and 1-(ferrocenyl)-1-(pyridin-2-yl)ethan-1-ol ([H]FePyalk, L4) to synthesize CuII complexes that vary in nuclearity and secondary coordination sphere. Also, the proligand 1-(ferrocenyl)-1-(5-methoxy-pyridin-2-yl)ethan-1-ol ([H]FeOMePyalk, L5) was synthesized with a substituted ; however, the isolation of a CuII complex ligated by L5 was not possible. Under variable reaction conditions, the pyalk ligands reacted with CuII precursors and formed either mononuclear or dinuclear CuII complexes depending on the amount of ligand added. The resulting complexes were characterized by single crystal X-ray diffraction, elemental analysis, and cyclic voltammetry.

Keywords: cyclic voltammetry ; ; electropolymerization ; electrochemistry ; multinuclear complexes ;

Purchased from AmBeed: ;

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Product Details of Benzophenone

CAS No. :119-61-9
Formula : C13H10O
M.W : 182.22
SMILES Code : O=C(C1=CC=CC=C1)C2=CC=CC=C2
Synonyms :
Diphenyl ketone; Benzoylbenzene; Diphenylmethanone
MDL No. :MFCD00003076
InChI Key :RWCCWEUUXYIKHB-UHFFFAOYSA-N
Pubchem ID :3102

Safety of Benzophenone

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H319-H373-H350-H411
Precautionary Statements:P501-P273-P260-P270-P202-P201-P264-P280-P391-P308+P313-P337+P313-P305+P351+P338-P301+P312+P330-P405
Class:9
UN#:3077
Packing Group:

Application In Synthesis of Benzophenone

* 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 [ 119-61-9 ]
  • Downstream synthetic route of [ 119-61-9 ]

[ 119-61-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 120569-14-4 ]
  • [ 1532-91-8 ]
  • [ 119-61-9 ]
  • [ 67-72-1 ]
  • [ 983-79-9 ]
References: [1] Tetrahedron Letters, 1988, vol. 29, # 48, p. 6287 - 6290.
  • 2
  • [ 34906-87-1 ]
  • [ 3060-50-2 ]
  • [ 119-61-9 ]
  • [ 57224-50-7 ]
  • [ 88319-43-1 ]
YieldReaction ConditionsOperation in experiment
62 % ee With C39H33N3O2*2ClH In methanol; water at 20℃; for 72 h; General procedure: To a 5 mL vial equipped with a magnetic stirrer bar were added 3-cyclohexyl-2-oxopropanoic acid (1j) (0.0510 g, 0.30 mmol), 2,2-diphenylglycine (2) (0.0681 g, 0.30 mmol), chiral pyridoxamine 6g (0.0195 g, 0.030 mmol), and MeOH-H2O (8:2) (3.0 mL). The mixture was stirred at 20 °C for 3 days. The reaction mixture was transferred to a 25 mL round-bottom flask and MeOH was added until all the solid was dissolved. Then silica gel (0.50 g) was added. After removal of the solvent in vacuo at 20 °C, the resulting residue was submitted to column chromatography on silica gel (EtOH/ethyl acetate/25-28percent ammonia solution =100:58:16) to give compound 3j (0.0401 g, 78percent yield, 52percent ee) as a white solid. The enantiomeric excesses of 3b-k were deteremined by HPLC analysis after being converted to N-benzoyl methyl esters by treatment with thionyl chloride in methanol and subsequent reaction benzoyl chloride.7 The enantiomeric excess of 3a was deteremined by HPLC analysis after being converted to its methyl ester by treatment with CH2N2 in methanol.
References: [1] Tetrahedron Letters, 2016, vol. 57, # 41, p. 4612 - 4615.
  • 3
  • [ 3027-05-2 ]
  • [ 630-19-3 ]
  • [ 3060-50-2 ]
  • [ 119-61-9 ]
  • [ 57224-50-7 ]
  • [ 88319-43-1 ]
References: [1] Tetrahedron Letters, 2016, vol. 57, # 41, p. 4612 - 4615.
  • 4
  • [ 34906-87-1 ]
  • [ 3060-50-2 ]
  • [ 119-61-9 ]
  • [ 57224-50-7 ]
  • [ 88319-43-1 ]
YieldReaction ConditionsOperation in experiment
62 % ee With C39H33N3O2*2ClH In methanol; water at 20℃; for 72 h; General procedure: To a 5 mL vial equipped with a magnetic stirrer bar were added 3-cyclohexyl-2-oxopropanoic acid (1j) (0.0510 g, 0.30 mmol), 2,2-diphenylglycine (2) (0.0681 g, 0.30 mmol), chiral pyridoxamine 6g (0.0195 g, 0.030 mmol), and MeOH-H2O (8:2) (3.0 mL). The mixture was stirred at 20 °C for 3 days. The reaction mixture was transferred to a 25 mL round-bottom flask and MeOH was added until all the solid was dissolved. Then silica gel (0.50 g) was added. After removal of the solvent in vacuo at 20 °C, the resulting residue was submitted to column chromatography on silica gel (EtOH/ethyl acetate/25-28percent ammonia solution =100:58:16) to give compound 3j (0.0401 g, 78percent yield, 52percent ee) as a white solid. The enantiomeric excesses of 3b-k were deteremined by HPLC analysis after being converted to N-benzoyl methyl esters by treatment with thionyl chloride in methanol and subsequent reaction benzoyl chloride.7 The enantiomeric excess of 3a was deteremined by HPLC analysis after being converted to its methyl ester by treatment with CH2N2 in methanol.
References: [1] Tetrahedron Letters, 2016, vol. 57, # 41, p. 4612 - 4615.
  • 5
  • [ 3027-05-2 ]
  • [ 630-19-3 ]
  • [ 3060-50-2 ]
  • [ 119-61-9 ]
  • [ 57224-50-7 ]
  • [ 88319-43-1 ]
References: [1] Tetrahedron Letters, 2016, vol. 57, # 41, p. 4612 - 4615.
  • 6
  • [ 5382-16-1 ]
  • [ 119-61-9 ]
  • [ 43076-61-5 ]
  • [ 90729-43-4 ]
YieldReaction ConditionsOperation in experiment
31 g
Stage #1: With aluminum (III) chloride; trifluorormethanesulfonic acid In toluene at 50℃; for 0.333333 h;
Stage #2: With toluene-4-sulfonic acid In water; toluene for 5 h; Reflux
Stage #3: With sodium hydrogencarbonate In water; toluene for 12 h; Reflux
The preparation method of ebastine provided in this embodiment specifically includes the following steps: (1) Add benzophenone (30 g, 0.165 mol) to 300 mL of toluene solution, stir and dissolve, aluminum trichloride (2.2 g, 0.017 mol) was added in sequence,trifluoromethanesulfonic acid (2.5 g, 0.018 mol),the mixture was heated to 50 ° C for 20 min, cooled to room temperature, p-toluenesulfonic acid (31.2 g, 0.18 mol) was added, 4-hydroxypiperidine (17.2 g, 0.17 mol) was added, and the mixture was heated to reflux, and refluxed with water for 5 h. After the reaction was completed, the reaction solution was cooled to room temperature, and 230 mL of 1N NaOH solution was slowly added thereto under ice cooling, and the mixture was stirred for 30 minutes, left to stand for 30 minutes, and the aqueous layer was separated. The organic layer was further added with sodium hydrogencarbonate (35 g, 0.41 mol). ,4-chloro-1-(4-tert-butylphenyl)-1-butanone (37.5 g, 0.157 mol), warmed to reflux, and refluxed with water for 12 h. After the reaction was completed, the temperature was lowered to room temperature and washed three times. , 200mL each time, wash to neutral.(2) The obtained organic solution was evaporated to the remaining 10percent volume, 100 mL of 95percent ethanol was added, the temperature was dissolved, the temperature was lowered to -10 ° C, and the crystal was frozen for 12 hours. The next day, the crystal was filtered off and dried to obtain ebastine (31g) 0.067mol), mp 84.2-86.3°C, total yield 40percent
References: [1] Patent: CN109593058, 2019, A, . Location in patent: Paragraph 0052-0064.
 

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