2-Phenylethanol is an aromatic alcohol with rose-like odor, slightly soluble in water, but miscible with most organic solvents, can be used as a food flavoring and fragrance ingredient.

Synonyms: Phenylethyl alcohol; Phenethyl alcohol; NSC 406252

4.5 *For Research Use Only !

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Quality Control of 2-Phenylethanol Purity: 95% SDS Specification

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Surveying the scope of aromatic decarboxylations catalyzed by prenylated-flavin dependent enzymes

Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto ; Prathamesh M. Datar ; Daniel J. DiRocco ; Katherine Huntera and E. Neil G. Marsh

DOI: 10.1039/D4FD00006D PubMed ID: 38837123 Faraday Discuss.,2024,252,208-222.

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ∼35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

Purchased from AmBeed: 27916-43-4 ; 2438-05-3 ; 501-89-3 ; 42287-94-5 ; 776-79-4 ; 53473-36-2 ; 7251-61-8 ; 42287-97-8 ; 1621-91-6 ; 37718-11-9 ; 288-13-1 ; 86-73-7 ; 104-53-0 ; 2018-90-8 ; 87-66-1 ; 135-19-3 ; 1664-57-9 ; 289-80-5 ; 693-95-8 ; 55-22-1 ; 102-93-2 ; 1477-50-5 ; 1632-76-4 ; 4780-79-4 ; 16642-79-8 ; 3581-89-3 ; 501-97-3 ; 771-50-6 ; 98-98-6 ; 619-64-7 ; 100-51-6 ; 402-45-9 ; 59-67-6 ; 93-60-7 ; 273-53-0 ; 2084-13-1 ; 51-17-2 ; 2459-09-8 ; 2459-07-6 ; 95-16-9 ; 459-31-4 ; 90-05-1 ; 150-76-5 ; 103-25-3 ; 271-44-3 ; 6293-56-7 ; 2550-26-7 ; 288-32-4 ; 501-52-0 ; 2001-32-3 ; 1592-38-7 ; 95-15-8 ; 91-19-0 ; 1122-61-8 ; 3724-19-4 ; 20173-24-4 ; 118-31-0 ; 6125-24-2 ; 60-12-8 ; 90-15-3 ; 120-72-9 ; 822-36-6 ; 288-47-1 ; 288-42-6 ; 2038-57-5 ; 38628-51-2 ; 1929-29-9 ; 15009-91-3 ; 1505-50-6 ; 581-40-8 ; 616-47-7 ; 1571-33-1

Investigations into Alcohol Functionalization via Barton-McCombie Type Deoxygenation

Chufan Andrew Jin ;

DOI: 10.17615/8bb9-3k97 University of North Carolina,2023.

Abstract: Reactive species that are employed as electrophiles in functionalization of substrates are typically prepared from native functionality such as alcohols and carboxylic acids. The addition of a pre-functionalization step of native substrates can reduce the efficiency of syntheses. These pre-functionalization reactions along with the functionalization reactions themselves proceed through polar mechanisms, limiting the scope of both functionalization and pre-functionalization reactions. Reported herein are preliminary efforts in the development of a deoxy-functionalization protocol for secondary and tertiary alcohols. The reported protocol proceeds through a derived Barton-McCombie deoxygenation mediated by a super silyl radical. Transfer of a thiocarbonate activating group to the silyl radical generates carbon radical which can be trapped out with an external sulfonyl trap, generating sulfonyl radical, which may then react with an allylic silane allowing for turnover of the radical chain.

Purchased from AmBeed: 206361-99-1 ; 60-12-8 ; 226700-81-8

Effect of passive cell immobilization of co-cultured yeasts on the whey fermentation and alcohols production

Valdez Castillo, Mariana ; Brar, Satinder Kaur ; Arriaga, Sonia ; Blais, Jean-Francois ; Avalos Ramirez, Antonio ;

DOI: 10.1016/j.jclepro.2022.133988 J. Clean. Prod.,2022,375,133988.

Abstract: Whey is one of the main residues of the dairy industry and its valorization by fermentation is an emergent practice that contributes to the circular economy and sustainable development. Whey fermentation with specialized yeast strains produces value-added biomols., such as fusel alcs. of high interest for the pharmaceutic, food and cosmetic industries due to their aromatic and flavor properties. The present study aimed to develop the whey fermentation with the yeasts Kluyveromyces marxianus and Debaryomyces hansenii immobilized on inert support, to increase cell d. and 2-phenylethanol (2-PE) production Biochar synthesized from wood feedstock, perlite and filter Kaldnes plastic rings were used as supports for the cell immobilization. They were selected based on their different nature and phys. properties such as porous structure and rough surface, to study the effect of different supports on yeast biofilm development. Also, functional groups such as hydroxyl, carbonyl, siloxane, and aliphatic hydrocarbons were useful for the development of covalent bonds and electrostatic forces between cells-support. The yeast immobilization increased the 2-PE production, especially on the plastic rings and perlite, obtaining 0.56 ± 0.01 g/L of 2-PE for the suspended culture and up to 0.91 ± 0.01 g/L for the immobilized co-culture on filter Kaldnes plastic rings.

Keywords: Whey fermentation ; Yeast immobilization ; Wood biochar ; Perlite ; Plastic rings ; 2-Phenylethanol production

Purchased from AmBeed: 60-12-8

Product Details of 2-Phenylethanol

CAS No. :	60-12-8
Formula :	C₈H₁₀O
M.W :	122.16
SMILES Code :	OCCC1=CC=CC=C1
Synonyms :	Phenylethyl alcohol; Phenethyl alcohol; NSC 406252
MDL No. :	MFCD00002886
InChI Key :	WRMNZCZEMHIOCP-UHFFFAOYSA-N
Pubchem ID :	6054

Safety of 2-Phenylethanol

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H313-H319
Precautionary Statements:	P264-P270-P280-P301+P312+P330-P305+P351+P338-P312-P337+P313-P501

Application In Synthesis of 2-Phenylethanol

* 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 [ 60-12-8 ]

[ 60-12-8 ] Synthesis Path-Downstream 1~53

1
[ 103-82-2 ]
[ 60-12-8 ]
[ 102-20-5 ]

Yield	Reaction Conditions	Operation in experiment
98.6%	With potassium hydroxide;	EXAMPLE 21 Preparation of 2-Phenylethyl Phenylacetate The product (98.6% pure by GLC) was prepared from 2-phenylethanol and phenylacetic acid by the method of Example 1: acid number, 0.16 mg KOH/g; saponification number, 231 mg KOH/g; refractive index, 1.5472; specific gravity, 1.081.
81%	With triphenylphosphine; benzyl azide; In neat (no solvent); at 140℃; for 0.166667h;Microwave irradiation;	General procedure: Toa mixture of triphenylphosphine (1.0 mmol), benzyl azide (1.0 mmol) was addedslowly in a 2-phenylethanol (1.0 mmol) and carboxylic acid (drop wise manner toavoid accumulation of azide) and the mixture was place to microwave at 140 Cfor 10 minutes. (Caution As azides are potentially explosive, all the reactionsshould be carried out behind a blast shield with personal protective equipment.In particular, the sequence of additionof the reactants should be strictly followed to avoid the accumulation of organicazides. This has been achieved in thepresent investigation by the slow drop wise addition of the benzyl azide to thereaction mixture containing triphenylphosphine during which the azide group isinstantaneous converted to iminophosphorane and hence no difficulty wasencountered). After the completion ofthe reaction (as monitored by TLC), the mixture was poured onto crushed ice. Then the reaction mixture was extracted withdichloromethane and the organic layer was dried over anhydrous Na2SO4. The solvent was removed and the residue waspurified by column chromatography using silica gel as the adsorbent andpetroleum ether:ethyl acetate (98:2) as the mobile phase to afford thecorresponding carboxylic esters (5ap) as colourless oily liquids. Yield (73-85%).
78%	With 1,3-diazido-propane; triphenylphosphine; In neat (no solvent); at 20℃; for 0.166667h;	General procedure: To a mixture of triphenylphosphine (1.0 mmol),2-phenylethanol/ cinnamyl alcohol (1.0 mmol) and carboxylic acid (1.0 mmol),1,3-diazidopropane (0.5mmol) was added slowly in a drop wise manner (to avoidaccumulation of azide) and the mixture was stirred at room temperature for 10minutes. (Caution As azides are potentially explosive, all thereactions should be carried out behind a blast shield with personal protectiveequipment. In particular, the sequenceof addition of the reactants should be strictly followed to avoid theaccumulation of organic azides. This hasbeen achieved in the present investigation by the slow drop wise addition ofthe bis azide to the reaction mixture containing triphenylphosphine duringwhich the azide group is instantaneous converted to iminophosphorane and henceno difficulty was encountered). Afterthe completion of the reaction (as monitored by TLC), the mixture was poured ontocrushed ice. Then the reaction mixturewas extracted with dichloromethane and the organic layer was dried overanhydrous Na2SO4.The solvent was removed and the residue was purified by columnchromatography using silica gel as the adsorbent and petroleum ether:ethylacetate (98:2) as the mobile phase to afford the corresponding carboxylicesters (5a-l) as colourless oilyliquids. Yield (77-85%).

References: [1]Patent: US2005/152858,2005,A1 .
[2]Journal of Organic Chemistry,2009,vol. 74,p. 5967 - 5974.
[3]Chemical Communications,2015,vol. 51,p. 3131 - 3134.
[4]Chemistry Letters,1984,p. 855 - 858.
[5]Tetrahedron Letters,2009,vol. 50,p. 4541 - 4544.
[6]Synthetic Communications,2016,vol. 46,p. 1454 - 1460.
[7]Tetrahedron Letters,2015,vol. 56,p. 6975 - 6979.
[8]Journal of the American Chemical Society,1925,vol. 47,p. 2243.
[9]Bulletin of the Chemical Society of Japan,1977,vol. 50,p. 1863 - 1866.

2
[ 103-82-2 ]
[ 60-12-8 ]
[ 102-20-5 ]

References: [1]Journal of Organic Chemistry,1959,vol. 24,p. 1847,1852.
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 10596 - 10599.
Angew. Chem.,2015,vol. 127,p. 10742 - 10745,4.

3
[ 60-12-8 ]
[ 102-20-5 ]

Yield	Reaction Conditions	Operation in experiment
27%	With calcium dichloride dihydrate; oxone; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; In dichloromethane; at 20℃; for 24h;	General procedure: The respective alcohol (1.0 mmol) was added to a suspension of Oxone (400.0 mg, m., CaCl2*2H2O (73.5 mg, 0.5 mmol) and TEMPO (1.6 mg, 0.01 mmol) in dichloromethane (2 mL). The reaction was initiated by the addition of 0.1 mL DI water. The reaction mixture was stirred at RT for the indicated times or until TLC or GC/MS showed consumption of the starting material and then filtered. After evaporation of the solvent using a rotavap, the crude reaction mixtures were separated via column chromatography to yield the desired ester dimers.

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1651 - 1653.
[2]Chemistry Letters,1983,p. 1097 - 1100.
[3]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 703 - 706.
[4]Chemical Communications,2019,vol. 55,p. 2797 - 2800.
[5]Journal of Organic Chemistry,1987,vol. 52,p. 4319 - 4327.
[6]Catalysis Communications,2013,vol. 40,p. 80 - 83.
[7]Tetrahedron Letters,2016,vol. 57,p. 2873 - 2876.
[8]Chemische Berichte,1900,vol. 33,p. 1723.
[9]Tetrahedron Letters,1981,vol. 22,p. 5327 - 5330.
[10]Journal of Organic Chemistry,1983,vol. 48,p. 1286 - 1292.
[11]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 2585 - 2588.
[12]Tetrahedron Letters,2006,vol. 47,p. 9199 - 9201.
[13]Journal of the American Chemical Society,2008,vol. 130,p. 17672 - 17673.
[14]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3045 - 3053.
[15]Journal of Organic Chemistry,2013,vol. 78,p. 6593 - 6598.
[16]Organometallics,2019,vol. 38,p. 1750 - 1760.

4
[ 4427-92-3 ]
[ 96-09-3 ]
[ 60-12-8 ]
[ 2979-22-8 ]
[ 122-78-1 ]
[ 103-29-7 ]

References: [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 1203 - 1204.

5
[ 60-12-8 ]
[ 13827-62-8 ]
Naphthalene-2,6-disulfonic acid diphenethyl ester [ No CAS ]

References: [1]Heterocycles,1993,vol. 36,p. 1715 - 1720.

6
[ 60-12-8 ]
[ 331-39-5 ]
[ 104594-70-9 ]
N,N'-dicyclohexyl-O-(3,4-dihydrocinnamoyl)isourea [ No CAS ]

References: [1]Russian Journal of Bioorganic Chemistry,1995,vol. 21,p. 124 - 131.
Bioorganicheskaya Khimiya,1995,vol. 21,p. 143 - 151.

7
[ 60-12-8 ]
[ 331-39-5 ]
[ 104594-70-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	With ytterbium(III) triflate; In nitromethane; at 120℃; for 0.666667h;Catalytic behavior;	To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol, 1.0 equiv.),alcohol (5.56 mmol, 1.0 equiv.) in nitromethane (125 mL) was addedytterbium triflate (34.4 mg, 0.056 mmol, 0.01 equiv.). After 5 min inan ultrasonic bath the mixture without protective gas was stirred ona 120 C oil bath for a given time. The reaction mixture was cooled toroom temperature, washed with deionised water (30 mL), 2% NaHCO3(30 mL) and brine, dried over anhydrous Na2SO4 and evaporated underreduced pressure to give the crude product, which was purified on asilica gel column to give the compounds 1-5 and 8-30.2-Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (1): Whitesolid; yield 758 mg, 48.0%; m.p. 128-130 C (lit.20 116-123 C);IR (KBr) numax 3480, 3328, 1683, 1601, 1362, 1301, 1279, 1182 cm-1;1H NMR (400 MHz, DMSO-d6) deltaH 7.46 (1H, d, J = 16 Hz, CH=CHCO),7.34-7.18 (5H, m, C6H5), 7.05 (1H, s, 2-ArH), 6.99 (1H, d, J = 8.0 Hz,6-ArH), 6.77 (1H, d, J = 8.0 Hz, 5-ArH), 6.24 (1H, d, J = 16 Hz,CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz,OCH2CH2) ppm; 13C NMR (100 MHz, DMSO-d6) deltaC 166.4, 148.3,145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8,64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M-H]- 283.0970, found283.0966.
48%	With ytterbium(III) triflate; In nitromethane; at 120℃;	General procedure: To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol), various phenethyl alcohols (5.56 mmol) in CH3NO2 (125 mL) was added Yb(OTf)3 (34.4 mg, 0.056 mmol). After 5 min of ultrasonic shake, the mixture was stirred on a 120 C oil bath for 40-120 min. The reaction mixture was cooled to room temperature, washed with 2% NaHCO3 (30 mL) and brine, dried over anhydrous Na2SO4, and concentrated to give crude products, which were purified by column chromatography to give the compounds 1-26 in 18-61% yields. Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (CAPE). White solid (48% yield for esterification reaction); Mp 128-130 C; 1H NMR (400 MHz, DMSO-d6) deltaH 7.46 (1H, d, J = 16.0 Hz, CH=CHCO), 7.34-7.18 (5H, m, C6H5), 7.05 (1H, s, 2-ArH), 6.99 (1H, d, J = 8.0 Hz, 5-ArH), 6.77 (1H, d, J = 8.0 Hz, 6-ArH), 6.24 (1H, d, J = 16.0 Hz, CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz, CH2C6H5) ppm; 13C NMR (100 MHz, DMSO-d6) deltaC 166.4, 148.3, 145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8, 64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M-H]- 283.0970, found 283.0966.
9%	With ytterbium(III) triflate; In nitromethane; for 1.5h;Reflux;	Caffeic acid (0.5 g, 2.78 mmol) and 2-phenylethanol (0.35 mL,2.78 mmol) were dissolved in nitromethane (62.5 mL). Yb(OTf)3(0.017 g, 0.028 mmol) was added, and the suspension was stirredfor 5 min in an ultrasonic bath followed by an additional 1.5 hstirring under reflux [4]. The reaction mixture was stirred at roomtemperature overnight and washed with NaHCO3-solution (2%,15 mL) and brine (15 mL). The organic phase was dried over Na2SO4and concentrated under reduced pressure. The crude product waspurified by column chromatography (silica gel; chloroform/methanol,99:1), and compound 17 was obtained as a white solid (0.07 g,9%); RF 0.04 (silica gel; chloroform/methanol, 99:1); m.p.128-130 C (lit.: [19]: 126-128 C); IR (KBr): nu 3480s, 1685m,1636m, 1602s, 1535w, 1442w, 1363w, 1302m, 1279s, 1182s cm1;UV-vis (CHCl3): lambda (log epsilon) 250 (4.06), 320 (4.21), 353 (4.28) nm; 1HNMR (500 MHz, CDCl3): delta 7.56 (d, J 15.9 Hz, 1H, 3-H), 7.34-7.30(m, 2H, 2-H), 7.27-7.22 (m, 3H, 3-H4-H), 7.07 (d, J 2.0 Hz, 1H, 50-H), 7.01 (dd, J 8.2, 2.0 Hz, 1H, 20-H), 6.87 (d, J 8.2 Hz, 1H, 60-H),6.25 (d, J 15.9 Hz, 1H, 2-H), 4.42 (t, J 7.1 Hz, 2H, 1-H), 3.01 (t,J 7.1 Hz, 2H, 2-H); 13C NMR (125 MHz, CDCl3): delta 167.8 (C-1),146.5 (C-40), 145.2 (C-30), 143.9 (C-3), 138.0 (C-1), 129.1 (C-3), 128.7(C-2), 127.7 (C-10), 126.8 (C-4), 122.7 (C-60), 115.7 (C-2), 115.6 (C-50),144.6 (C-20), 65.3 (C-1), 35.4 (C-2) ppm; MS (ESI, MeOH): m/z(%) 285.0 ([MH], 45), 302.2 ([MNH4], 23), 307.1 ([MNa],100), 446.1 ([3 MKH]2, 44), 580.1 ([4 MNaH]2, 23), 588.0([4MKH]2, 50), 590.8 ([2MNa], 42), 599.9 ([4MZn]2, 48);analysis calcd for C17H16O4 (284.31): C 71.82, H 5.67; found: C 71.69,H 5.83.

	With toluene-4-sulfonic acid; In benzene;	Synthesis of Cinnamic Acid Analogues. The synthesis of cinnamic acid analogues was achieved by straight forward application of literature techniques. Two general approaches, designated "method A" and "method B" were utilized: Method A: Synthesis of Caffeic acid beta-phenylethyl ester (CAPE, 67H-42-A). A solution of 1.80 g (10.0 mmol) of caffeic acid, 17.9 mL (150 mmol) of beta-phenylethyl alcohol and 100 mg of p-toluenesulfonic acid in benzene (100 mL) were stirred overnight at reflux with a Dean Stark trap. Solvent and excess alcohol were removed by distillation and residue purified by silica gel chromatography (petroleum ether/CHCl3). Product was crystallized (ether/petroleum ether) to provide 67H-42-A as snow-white crystals, 1.0 g (35%): mp 128.0 C. 126-128 C.) (Grunberger, D. et al., Experimentia, (1988) 44:230-2).
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 48h;	General procedure: Cinnamicacid esters (13-22) were synthesized according to a modified previous procedure.31) To a mixture of cinnamic acid derivatives (Ia-d, 3.0 mmol) and the appropriate alcohol (2.0 mmol)in dry tetrahydrofuran (6mL) were added triphenylphosphine (3.0 mmol) and diisopropyl azodicarboxylate (DIAD(3.0mmol). The reaction mixture was stirred for 48h at room temperature and the whole mixture was extracted with AcOEt and saturated NaHCO3 solution, and the organic extract was washed with brine.The organic layer was dried overNa2SO4 and the solvent was evaporated under reduced pressure. The residue was then purified by silica gel column chromatography (hexane:AcOEt=2:1)to give the title compound.

References: [1]Patent: EP1211237,2002,A1 .Location in patent: Example 1.
[2]Organic Letters,2002,vol. 4,p. 3839 - 3841.
[3]Journal of Chemical Research,2014,vol. 38,p. 695 - 700.
[4]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 131 - 134.
[5]Patent: EP1211237,2002,A1 .Location in patent: Page 5.
[6]Patent: EP1211237,2002,A1 .Location in patent: Page 5.
[7]Journal of Medicinal Chemistry,1995,vol. 38,p. 4171 - 4178.
[8]European Journal of Medicinal Chemistry,2019,vol. 177,p. 259 - 268.
[9]Patent: US5610185,1997,A .
[10]Chemical and Pharmaceutical Bulletin,2017,vol. 65,p. 1020 - 1027.
[11]Journal of Agricultural and Food Chemistry,2019,vol. 67,p. 2028 - 2035.

8
[ 60-12-8 ]
[ 100-27-6 ]
[ 15121-84-3 ]
[ 52022-77-2 ]

References: [1]Russian Journal of Organic Chemistry,1994,vol. 30,p. 1556 - 1558.
Zhurnal Organicheskoi Khimii,1994,vol. 30,p. 1478 - 1480.
[2]Russian Journal of Organic Chemistry,1994,vol. 30,p. 1556 - 1558.
Zhurnal Organicheskoi Khimii,1994,vol. 30,p. 1478 - 1480.

9
[ 60-12-8 ]
[ 536-74-3 ]
[ 103-82-2 ]
[ 102-20-5 ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 7728 - 7732.

10
[ 60-12-8 ]
[ 102-20-5 ]
[ 122-78-1 ]

Yield	Reaction Conditions	Operation in experiment
58.7%; 41.3%	With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; iodine; sodium hydrogencarbonate; In dichloromethane; water; at 20 - 25℃; for 3h;	General procedure: A mixture of 10 mL of 0.1 mol/L solution of sodium hydrocarbonate and 0.084 g (0.4 mmol) of compound 1 were charged into a 50 mL flat-bottom flask equipped with a reflux condenser and a magnetic stirrer. 4 mmol of an alcohol dissolved in 10 mL of methylene chloride (alcohol-nitroxyl 1 molar ratio1 : 0.1) was added to the solution, and then 0.4 mmolof an amine was introduced (alcohol-amine 1 : 0.1; 1-amine 1 : 1). 2.0 g (8 mmol) of crystalline iodine was added at vigorous stirring to the two-phase system; the mixture was stirred during 3 h at 20-25 and then treated with 20% solution of sodium thiosulfate for elimination of excess iodine. Aqueous and organic layers were separated, and the product was additionally extracted from the aqueous layer with methylene chloride (2×10 mL). The organic phases were combined and analyzed by means of chromatography.
71%Chromat.; 23%Chromat.	With pyridine; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; iodine; sodium hydrogencarbonate; In dichloromethane; water; at 20 - 22℃; for 3h;Catalytic behavior;	General procedure: A solution of alcohol 1a-c,j,l,p (4.0 mmol), nitroxide 4a (42.6 mg, 0.2 mmol) and compound 6a-d (0.4 mmol) in CH2Cl2 (10 mL) was added to a magnetically stirred solution of NaHCO3 (1.0 g, 11.94 mmol)in water (10 mL) at 20-22 C, then I2 (2.02 g, 7.96 mmol) powder was added in one portion to the formed two-phase mixture. The reaction mixture was stirred at 20-22 C for appropriate time (Table S07). Then a saturated solution of sodium thiosulfate (3 mL) was added and the resulted mixture was stirred for 5 min, organic and aqueous phases were separated and analyzed by GC-MS of HPLC (Table S07).
12%Chromat.; 86%Chromat.	With 2,6-dimethylpyridine; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; iodine; sodium hydrogencarbonate; In dichloromethane; water; at 20 - 22℃; for 3h;Catalytic behavior;	General procedure: A solution of alcohol 1a-c,j,l,p (4.0 mmol), nitroxide 4a (42.6 mg, 0.2 mmol) and compound 6a-d (0.4 mmol) in CH2Cl2 (10 mL) was added to a magnetically stirred solution of NaHCO3 (1.0 g, 11.94 mmol)in water (10 mL) at 20-22 C, then I2 (2.02 g, 7.96 mmol) powder was added in one portion to the formed two-phase mixture. The reaction mixture was stirred at 20-22 C for appropriate time (Table S07). Then a saturated solution of sodium thiosulfate (3 mL) was added and the resulted mixture was stirred for 5 min, organic and aqueous phases were separated and analyzed by GC-MS of HPLC (Table S07).

References: [1]Journal of Organic Chemistry,1998,vol. 63,p. 9367 - 9374.
[2]Russian Journal of General Chemistry,2016,vol. 86,p. 2423 - 2426.
Zh. Obshch. Khim.,2016,vol. 86,p. 1779 - 1783,5.
[3]Catalysis Communications,2011,vol. 13,p. 82 - 86.
[4]Tetrahedron Letters,2017,vol. 58,p. 3517 - 3521.
[5]Tetrahedron Letters,2017,vol. 58,p. 3517 - 3521.

11
[ 96-09-3 ]
[ 67-56-1 ]
[ 60-12-8 ]
[ 2979-22-8 ]

References: [1]Chemical Communications,1999,p. 1041 - 1042.

12
[ 96-09-3 ]
[ 60-12-8 ]
[ 2979-22-8 ]

References: [1]Chemical Communications,1999,p. 1041 - 1042.

13
[ 103-82-2 ]
rhenium [ No CAS ]
[ 60-12-8 ]
[ 102-20-5 ]

References: [1]Journal of Organic Chemistry,1959,vol. 24,p. 1847,1852.

14
[ 60-12-8 ]
[ 7664-93-9 ]
dichromate [ No CAS ]
[ 102-20-5 ]
[ 100-52-7 ]
[ 64-19-7 ]
[ 65-85-0 ]

References: [1]Chemische Berichte,1900,vol. 33,p. 1723.

15
[ 3471-31-6 ]
[ 60-12-8 ]
(5-methoxy-1<i>H</i>-indol-3-yl)-acetic acid phenethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2860 - 2870.

16
[ 2882-15-7 ]
[ 60-12-8 ]
[ 288854-00-2 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2860 - 2870.

17
[ 60-12-8 ]
[ 54925-64-3 ]
[ 78926-09-7 ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,2000,vol. 166,p. 71 - 81.

18
[ 60-12-8 ]
[ 77201-71-9 ]
[ 104594-70-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 3351 - 3359.
[2]Patent: EP1211237,2002,A1 .Location in patent: Page 5.

19
[ 381-98-6 ]
[ 60-12-8 ]
[ 252061-10-2 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 2499 - 2502.

20
[ 60-12-8 ]
[ 75-64-9 ]
[ 102-20-5 ]
[ 24070-10-8 ]

References: [1]Chemical Communications,2007,p. 725 - 727.
[2]Chemical Communications,2007,p. 725 - 727.

21
[ 60-12-8 ]
[ 104594-70-9 ]

References: [1]Journal of Chemical Research,2006,p. 586 - 588.
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4367 - 4371.
[3]Bioorganic Chemistry,2019,vol. 86,p. 686 - 695.

22
[ 60-12-8 ]
[ 6628-68-8 ]

References: [1]Journal of the American Chemical Society,1924,vol. 46,p. 2845.
[2]Annales de Chimie (Cachan, France),1938,vol. <11> 9,p. 5,82.
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1936,vol. 202,p. 1679.

23
[ 60-12-8 ]
[ 15121-84-3 ]

References: [1]Bulletin de la Societe Chimique de France,1933,vol. <4> 53,p. 330,332.

24
[ 60-12-8 ]
[ 5337-63-3 ]

References: [1]Journal of the Chemical Society,1931,p. 1336,1340.

25
[ 60-12-8 ]
[ 939-57-1 ]
phenylethyl o-methylcinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In water; toluene;	EXAMPLE 4 Phenylethyl o-methylcinnamate A solution of 324.0 g (2.00 moles) of o-methylcinnamic acid, 428.0 g (3.5 moles) of 2-phenylethanol, 10.0 g (0.058 moles) of p-toluenesulfonic acid and 1,200 ml of toluene was refluxed under a water separator. After 15 hours, the calculated amount of water had separated off. The reaction solution was washed first with water and then with saturated sodium bicarbonate solution. The combined washwater was extracted once with ether, and the ether phase was combined with the organic phase. The combined, organic phases were fractionated over a 10 cm Vigreux column. The solvents were separated off under atmospheric pressure and in a vacuum from a water pump. The Vigreux column was replaced by a column head and the product was distilled under 0.01 mm Hg (b.p. 154-155 C./0.01 mm Hg). 394.0 g of phenylethyl o-methylcinnamate of melting point 52 to 53 C. were obtained.

References: [1]Patent: US5066640,1991,A .

26
[ 112-30-1 ]
[ 112-53-8 ]
[ 107-92-6 ]
[ 137-66-6 ]
[ 60-12-8 ]

Yield	Reaction Conditions	Operation in experiment
		b) a mixture consisting of 9 g of decanol, 1.0 g of dodecanol added with 1% ascorbyl palmitate, butyric acid (2.0 g), phenylethyl alcohol (6.0 g) is prepared;

References: [1]Patent: EP1270007,2003,A2 .

27
[ 60-12-8 ]
[ 51843-24-4 ]
3-Acetyl-5-chloro-1-phenethylindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With diisopropyl (E)-azodicarboxylate; triphenylphosphine; In tetrahydrofuran;	(1) To a mixture of 0.58 g (3 mmol) of <strong>[51843-24-4]3-acetyl-5-chloroindole</strong>, 1.42 g (5.4 mmol) of triphenylphosphine and 0.66 g (5.4 mmol) of phenethyl alcohol in THF (12 ml) was added under ice-cooling, 1.09 g (5.4 mmol) of diisopropyl azodicarboxylate. After stirring for 3 hours at room temperature, the mixture was concentrated under reduced pressure. The obtained residue was chromatographed on silica gel (1/4 ethyl acetate/toluene as eluant) to give 0.58 g of the titled compound as an oil. Yield: 65%. NMR(CDCl3) delta: 2.38(1H, s), 3.12(2H, t, J=7.2 Hz), 4.36(2H, t, J=7.2 Hz), 6.97-7.01(2H, m), 7.20-7.30(5H, m), 7.38(1H, s), 8.38(1H, d, J=1.8 Hz).

References: [1]Patent: US6333323,2001,B1 .

28
[ 60-12-8 ]
[ 120870-47-5 ]
[ 1093198-48-1 ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 7046 - 7049.

29
[ 60-12-8 ]
[ 39207-65-3 ]
[ 1241621-67-9 ]
[ 103-48-0 ]

References: [1]Chemistry - An Asian Journal,2010,vol. 5,p. 941 - 945.

30
[ 60-12-8 ]
[ 7768-28-7 ]
[ 13398-94-2 ]

References: [1]Journal of Molecular Catalysis B: Enzymatic,2010,vol. 66,p. 72 - 80.

31
[ 60-12-8 ]
[ 102-20-5 ]
[ 108-88-3 ]

References: [1]Organometallics,2011,vol. 30,p. 6044 - 6048.

32
[ 60-12-8 ]
[ 142-84-7 ]
[ 102-20-5 ]
[ 25173-09-5 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 10005 - 10010.

33
[ 60-12-8 ]
[ 103-49-1 ]
[ 102-20-5 ]
[ 102459-18-7 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 10005 - 10010.

34
[ 60-12-8 ]
[ 520-26-3 ]
[ 88510-08-1 ]

References: [1]Journal of Agricultural and Food Chemistry,2011,vol. 59,p. 11238 - 11243.

35
[ 102-20-5 ]
[ 60-12-8 ]

References: [1]European Journal of Organic Chemistry,2013,p. 2061 - 2065.
[2]Organometallics,2013,vol. 32,p. 5581 - 5588.

36
[ 60-12-8 ]
[ 100-51-6 ]
[ 102-16-9 ]
[ 120-51-4 ]
[ 94-47-3 ]
[ 102-20-5 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 6593 - 6598.

37
[ 98-85-1 ]
[ 60-12-8 ]
[ 102-20-5 ]
[ 98-86-2 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 6593 - 6598.

38
[ 85426-79-5 ]
[ 60-12-8 ]
[ 1338789-21-1 ]

References: [1]ACS Combinatorial Science,2014,vol. 16,p. 168 - 175.

39
[ 103-82-2 ]
[ 599-67-7 ]
[ 60-12-8 ]
[ 555-16-8 ]
[ 123-11-5 ]
[ 104-94-9 ]
[ 126-30-7 ]
[ 530-48-3 ]
[ 5455-87-8 ]
[ 6290-08-0 ]
[ 102-20-5 ]
[ 1749-08-2 ]