5581-75-9

Basic information

• Product Name: 6-PHENYLHEXANOIC ACID
• Synonyms: 6-Phenylhexanoic acid,99%;NSC 66179;RARECHEM AH CK 0156;BENZENEHEXANOIC ACID;6-PHENYLHEXANOIC ACID;6-Phenylhexanoic acid 98%;6-Phenylhexanoic acid, 98+%;6-Phenylcaproic acid
• CAS NO: 5581-75-9
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 5581-75-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 17-19°C
• Boiling Point: 201-202 °C24 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White Solid
• Density: 1.022 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000144mmHg at 25°C
• Refractive Index: n20/D 1.51(lit.)
• Solubility: Difficult to mix.
• PKA: 4.78±0.10(Predicted)
• Water Solubility: 479.8mg/L(30 oC)
• BRN: 1950106
• CAS DataBase Reference: 6-PHENYLHEXANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-PHENYLHEXANOIC ACID(5581-75-9)
• EPA Substance Registry System: 6-PHENYLHEXANOIC ACID(5581-75-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 5581-75-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 5581-75-9 differently. You can refer to the following data:
1. 6-Phenylhexanoic Acid (cas# 5581-75-9) is a compound useful in organic synthesis.
2. 6-Phenylhexanoic acid was employed as a model compound to investigate the effects of chromophore orientation and molecular conformation on surface-enhanced Raman scattering based on metal nanostructures. It was also employed as a substrate to study the stoichiometry of side chain metabolism or complete mineralization of surrogate napthenic acids under methanogenic conditions.

General Description

6-Phenylhexanoic acid is an arylalkanoic acid.

InChI:InChI=1/C12H16O2/c13-12(14)10-6-2-5-9-11-7-3-1-4-8-11/h1,3-4,7-8H,2,5-6,9-10H2,(H,13,14)/p-1

Synthetic route

trans 6-phenyl-5-hexenoic acid (16424-56-9) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate at 25℃; under 1551.4 Torr; for 1h;	95%
With platinum(IV) oxide; hydrogen In tetrahydrofuran at 20℃; for 1h;

6-phenyl-1-hexanol (2430-16-2) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With palladium 10% on activated carbon; water; sodium hydrogencarbonate at 80℃; under 600.06 Torr; for 9h; Reagent/catalyst; Time;	95%

1-Diazo-6-phenylhexan-2-one (129866-61-1) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With lithium perchlorate In acetonitrile at 26.85℃; Wolff rearrangement; Electrochemical reaction;	94%
With silver nanocluster In 1,4-dioxane; water at 60℃;	92%

glutaric anhydride, (108-55-4) + 1-phenyl-2-bromoethane (103-63-9) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0); zinc In N,N-dimethyl acetamide at 80℃; for 12h;	90%

(RS)-2-phenylcyclohexanone (1444-65-1) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With oxygen; vanadium(V) oxychloride In acetic acid at 65℃; for 52h;	81%
With potassium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene Reflux;	78%

6-phenyl-1-hexanol (2430-16-2) → pentylbenzene (538-68-1) + 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With 10% rhodium on carbon; water; sodium hydroxide at 100℃; under 675.068 Torr; for 6h; Pressure;	A 11% B 80%

C14H17Cl3O2 → 6-phenylhexanoic acid 2,2-dichloroethyl ester + 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With indium; ammonium chloride In tetrahydrofuran for 24h; Heating;	A 60% B 27%

6-oxo-6-phenyl-hexanoic acid methyl ester (21876-11-9) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With hydrazine hydrate	56%
Multi-step reaction with 2 steps 1: aq. NaOH / acetone / 25 °C / other temp., ΔΔH excit., ΔΔS excit. View Scheme

carbon dioxide (124-38-9) + 2-bromo-5-phenylpentane (63789-86-6, 65511-83-3, 143097-81-8, 143097-84-1) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With rubidium carbonate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; (6,6’-dimethyl-2,2'-bipyridine)nickel(II) dibromide In N,N-dimethyl-formamide at 10℃; under 750.075 Torr; for 20h; Schlenk technique; Sealed tube; Irradiation;	52%

6-phenyl-1-hexanol (2430-16-2) → pentylbenzene (538-68-1) + 6-phenylhexanic acid (5581-75-9) + 1-pentenylbenzene (826-18-6)

Conditions	Yield
With 10% rhodium on carbon; sodium hydroxide In water at 100℃; for 24h; Inert atmosphere;	A n/a B 50% C n/a

6-phenyl-1-hexanol (2430-16-2) → 6-phenylhexanic acid (5581-75-9) + 6-phenylhexanal (16387-61-4)

Conditions	Yield
With palladium 10% on activated carbon; water; sodium hydrogencarbonate at 80℃; under 600.06 Torr; for 6h;	A 19% B 7%

sodium diethylmalonate (996-82-7, 34727-00-9, 73177-21-6) + 1-Bromo-4-phenylbutane (13633-25-5) → 6-phenylhexanic acid (5581-75-9)

5-benzylthiophene-2-carboxylic acid (13132-16-6) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With alkaline solution; nickel

6-phenylhexanenitrile (17777-31-0) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With potassium hydroxide

5-benzoylvaleric acid (4144-62-1) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With hydrogenchloride; amalgamated zinc Verseifung und Behandlung des Reaktionsprodukts mit Wasserstoff in Alkohol bei Gegenwart von kolloidalem Palladium;
With hydrogenchloride; mercury; zinc
With triethylsilane; trifluoroacetic acid

rac-(2-phenylbutyl)propanedioic acid (97025-01-9) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
at 160℃;

4-oxo-6-phenylhexanoic acid (13122-67-3) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With hydrogenchloride; amalgamated zinc

ethyl 6-oxo-6-phenylhexanoate (4248-25-3) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol

6-phenyl-hexanoic acid methyl ester (5581-76-0) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With sodium hydroxide In acetone at 25℃; Kinetics; Thermodynamic data; other temp., ΔH excit., ΔS excit.;
With sodium hydroxide In tetrahydrofuran; water at 20℃;	541 mg

peracide phenyl-6 hexanoique (62103-18-8) → phenyl butyl ketone (1009-14-9) + 1-Phenyl-1-pentanol (583-03-9) + 5-phenylpentan-1-ol (10521-91-2) + 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
In n-heptane at 98℃; Further byproducts given;	A 0.01 mol B 0.19 mol C 0.20 mol D 0.18 mol

peracide phenyl-6 hexanoique (62103-18-8) → phenyl butyl ketone (1009-14-9) + 1-Phenyl-1-pentanol (583-03-9) + 5-phenylpentan-1-ol (10521-91-2) + 6-phenylhexanic acid (5581-75-9) + 5-Phenylpentanoic acid (2270-20-4)

Conditions	Yield
In n-heptane at 98℃; Mechanism; Product distribution;	A 0.01 mol B 0.19 mol C 0.20 mol D 0.18 mol E 0.01 mol

peracide phenyl-6 hexanoique (62103-18-8) → 1-Phenyl-1-pentanol (583-03-9) + 5-phenylpentan-1-ol (10521-91-2) + 6-phenylhexanic acid (5581-75-9) + 5-Phenylpentanoic acid (2270-20-4)

Conditions	Yield
In n-heptane at 98℃; Further byproducts given;	A 0.19 mol B 0.20 mol C 0.18 mol D 0.01 mol

peracide phenyl-7 heptanoique (62103-19-9) → 6-phenyl-1-hexanol (2430-16-2) + 6-phenylhexanic acid (5581-75-9) + 7-phenylheptanoic acid (40228-90-8) + 1-phenyl-2-hexanone (25870-62-6) + 1-phenylhexan-1-ol (4471-05-0) + (+/-)-1-phenylhexan-2-ol (25755-72-0)

Conditions	Yield
In hexane at 69℃; Mechanism; Product distribution;	A 0.38 mol B 0.02 mol C 0.27 mol D n/a E 0.13 mol F 0.04 mol

peracide phenyl-7 heptanoique (62103-19-9) → 6-phenyl-1-hexanol (2430-16-2) + 6-phenylhexanic acid (5581-75-9) + 7-phenylheptanoic acid (40228-90-8) + 1-phenylhexan-1-ol (4471-05-0)

Conditions	Yield
In hexane at 69℃; Further byproducts given;	A 0.38 mol B 0.02 mol C 0.27 mol D 0.13 mol

6-chlorohexanoic acid (4224-62-8) + benzene (71-43-2) → 6-phenylhexanic acid (5581-75-9) + 4-phenylhexanoic acid (5354-04-1) + 5-phenylhexanoic acid (2972-25-0)

Conditions	Yield
With aluminium trichloride Product distribution; degree of isomerization of the alkyl chain;	A 42 % Chromat. B 1 % Chromat. C 57 % Chromat.

5-oxo-6-phenylhexanoic acid (40564-60-1) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With hydrazine Heating;

d-benzyl-levulinic acid → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
With sodium ethanolate; hydrazine hydrate at 180℃;

hydrogenchloride (7647-01-0) + ethyl 6-oxo-6-phenylhexanoate (4248-25-3) + amalgamated zinc → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
Verseifen des Reaktionsprodukts;

methyl adipoyl chloride (35444-44-1) → 6-phenylhexanic acid (5581-75-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 53 percent 2: 56 percent / hydrazine hydrate, base View Scheme
Multi-step reaction with 3 steps 1: 77 percent / AlCl3 2: aq. NaOH / acetone / 25 °C / other temp., ΔΔH excit., ΔΔS excit. View Scheme

methanol (67-56-1) + 6-phenylhexanic acid (5581-75-9) → 6-phenyl-hexanoic acid methyl ester (5581-76-0)

Conditions	Yield
With chloro-trimethyl-silane at 0 - 20℃; for 4h; Inert atmosphere;	100%
trioctyl(propyl-3-sulfonic acid)ammonium bis(trifluoromethylsulfonyl)imide In water at 90℃; for 24h;	80%
With chloro-trimethyl-silane at 0℃;	2.88 g
With hydrogenchloride In methanol for 24h; Heating / reflux;
With sulfuric acid for 3h; Reflux;

6-phenylhexanic acid (5581-75-9) + N-butyl-3-formamido-2-hydroxybenzamide (2843-26-7) → N-butyl-2-hydroxy-3-(6-phenylhexanamido)benzamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 15h; Inert atmosphere;	99%

diazomethane (186581-53-3, 908094-01-9) + 6-phenylhexanic acid (5581-75-9) → 6-phenyl-hexanoic acid methyl ester (5581-76-0)

Conditions	Yield
In diethyl ether at 20℃; for 1h; Inert atmosphere;	96%

6-phenylhexanic acid (5581-75-9) → 6-phenylhexanoyl chloride (21389-46-8)

Conditions	Yield
With thionyl chloride	94%
With phosphorus pentachloride
With thionyl chloride; benzene

6-phenylhexanic acid (5581-75-9) → hexylbenzene (1077-16-3)

Conditions	Yield
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃;	93%
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 20h;	93%

6-phenylhexanic acid (5581-75-9) + 2-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-1,2,3-triazol-4-yl)-7-azabicyclo[2.2.1]heptane → 1-(2-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-1,2,3-triazol-4-yl)-7-azabicyclo[2.2.1]heptan-7-yl)-6-phenylhexan-1-one

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;	91.6%

6-phenylhexanic acid (5581-75-9) → 6-phenyl-1-hexanol (2430-16-2)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 25℃; for 4h;	91%
Multi-step reaction with 2 steps 1: 2.88 g / TMSCl / 0 °C 2: 76 percent / DIBAL-H / tetrahydrofuran; toluene / 2 h / 0 °C View Scheme
With diborane In tetrahydrofuran

6-phenylhexanic acid (5581-75-9) → C12H15O5S(1-)*0.5Ca(2+)

Conditions	Yield
With sulfuric acid at 100℃; for 2h;	85%

6-phenylhexanic acid (5581-75-9) + (2S,3S,4R)-2-amino-3,4-di-O-benzyl-1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)octadec-6-ene-1,3,4-triol (1541195-83-8) → (2S,3S,4R)-3,4-di-O-benzyl-1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-(6-phenylhexanoylamino)octadec-6-ene-1,3,4-triol (1541195-84-9)

Conditions	Yield
Stage #1: 6-phenylhexanic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide for 0.5h; Stage #2: (2S,3S,4R)-2-amino-3,4-di-O-benzyl-1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)octadec-6-ene-1,3,4-triol With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 18h;	85%

6-phenylhexanic acid (5581-75-9) → ((1R,5S)-1-(3-methylbut-2-en-1-yl)-7-oxo-6-oxabicyclo[3.2.0]hept-2-en-3-yl)methyl-6-phenylhexanoate

Conditions	Yield
With thionyl chloride In dichloromethane at 20℃; for 5h; Inert atmosphere;	85%

6-phenylhexanic acid (5581-75-9) + C28H44N4O8*C2HF3O2 → C40H58N4O9

Conditions	Yield
Stage #1: 6-phenylhexanic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: C28H44N4O8*C2HF3O2 With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	84%

6-phenylhexanic acid (5581-75-9) + 2-hydroxymethyl-18-crown-6 (70069-04-4) → (1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methyl 6-phenylhexanoate

Conditions	Yield
With dmap; silica gel; dicyclohexyl-carbodiimide at 20℃; for 24h; Steglich Esterification; Inert atmosphere;	79%

6-phenylhexanic acid (5581-75-9) + trans-4-hydroxycyclohexylamine (27489-62-9) → N-(trans-4-hydroxycyclohexyl)-6-phenylhexanamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 16h;	77.8%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 10℃; for 10h;	15.3%

tert-butyl (4-aminocyclohexyl)carbamate (195314-59-1) + 6-phenylhexanic acid (5581-75-9) → tert-butyl (4-(6-phenylhexanamido)cyclohexyl)carbamate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 12h;	77.4%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 6-phenylhexanic acid (5581-75-9) → C16H19NO4 (1217298-52-6)

Conditions	Yield
With dicyclohexyl-carbodiimide at 0 - 20℃; for 8.5h;	76%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux;

6-phenylhexanic acid (5581-75-9) + 1-(tert-butoxycarbonyl)-4-aminopiperidine (87120-72-7) → C22H34N2O3

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 12h;	76%

6-phenylhexanic acid (5581-75-9) → 7,8,9,10-tetrahydro-6H-benzocycloocten-5-one (829-14-1)

Conditions	Yield
Stage #1: 6-phenylhexanic acid With oxalyl dichloride In dichloromethane at 0 - 20℃; for 14h; Stage #2: With aluminum (III) chloride In dichloromethane for 20.5h; Inert atmosphere;	75%
With PPA
Multi-step reaction with 2 steps 1: SOCl2 2: AlCl3 / CS2 View Scheme
With oxalyl dichloride In dichloromethane at 0 - 20℃; for 1h;

6-(8-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-pyridine-2-sulfonamide (1135871-90-7) + 6-phenylhexanic acid (5581-75-9) → N-(6-phenyl-hexanoyl)-6-(8-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-pyridine-2-sulfonamide (1135871-94-1)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;	75%

6-phenylhexanic acid (5581-75-9) + C18H17Cl2N5 (1431331-65-5) → C30H31Cl2N5O (1431331-43-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 20h;	75%

6-phenylhexanic acid (5581-75-9) + 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-aminoindol-1-yl)-2-butyl]imidazole-4-carboxamide (294862-31-0) → 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(6-phenylhexanoylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide (294862-54-7)

Conditions	Yield
Stage #1: 6-phenylhexanic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 0.666667h; Stage #2: 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-aminoindol-1-yl)-2-butyl]imidazole-4-carboxamide In dichloromethane at 20℃; for 4h;	74.8%

phenyl sulfamate (19792-91-7) + 6-phenylhexanic acid (5581-75-9) → phenyl (6-phenylhexanoyl)sulfamate (1393590-22-1)

Conditions	Yield
Stage #1: 6-phenylhexanic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 0.75h; Inert atmosphere; Stage #2: phenyl sulfamate With dmap; triethylamine In dichloromethane; N,N-dimethyl-formamide Inert atmosphere;	74%

(3,5-dichloropyridin-4-yl)hydrazine (153708-69-1) + 6-phenylhexanic acid (5581-75-9) → N'-(3,5-dichloropyridin-4-yl)-6-phenylhexanehydrazide (1370286-94-4)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	71%

6-phenylhexanic acid (5581-75-9) → (E)-6-phenyl-2-hexenoic acid (84299-18-3)

Conditions	Yield
Stage #1: 6-phenylhexanic acid With Zn(2,2,6,6-tetramethylpiperidine)2*2LiCl In tetrahydrofuran at -40℃; for 1.5h; Inert atmosphere; Sealed tube; Stage #2: With bis(η3-allyl-μ-chloropalladium(II)); Allyl acetate In tetrahydrofuran at -40 - 60℃; for 3h; Inert atmosphere; Sealed tube; diastereoselective reaction;	69%

6-phenylhexanic acid (5581-75-9) + cis-4-aminocyclohexanol (6850-65-3, 27489-62-9, 40525-78-8) → N-(cis-4-hydroxycyclohexyl)-6-phenylhexanamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 16h;	67.4%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 10℃; for 10h;	15.3%

Upstream product

• 13132-16-6 5-benzylthiophene-2-carboxylic acid 
• 17777-31-0 6-phenylhexanenitrile 
• 4224-62-8 6-chlorohexanoic acid 
• 71-43-2 benzene 
• 2430-16-2 6-phenyl-1-hexanol 
• 4144-62-1 5-benzoylvaleric acid 
• 97025-01-9 rac-(2-phenylbutyl)propanedioic acid 
• 108-55-4 glutaric anhydride, 
• 103-63-9 1-phenyl-2-bromoethane 
• 141632-24-8 7-phenyloxepan-2-one 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 1589-60-2 1-phenylcyclohexanol 
• 626-86-8 adipinic acid monoethyl ester 
• 1071-71-2 ethyl 6-chloro-6-oxohexanoate 

Downstream Products

• 35402-72-3 N-Phenacyl-glycin 
• 88343-63-9 2-(6-phenyl-1-oxohexyl)thiophene 
• 141632-24-8 7-phenyloxepan-2-one 
• 19629-78-8 16-phenyl-hexadecanoic acid 
• 106181-23-1 16-phenylhexadecanoic acid methyl ester 
• 106181-16-2 6-(5-(6-Phenylhexanoyl)-2-thienyl)hexanoic Acid 
• 106181-17-3 6-{5-[2-(5-Phenyl-pentyl)-[1,3]dithiolan-2-yl]-thiophen-2-yl}-hexanoic acid 
• 179060-54-9 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one 
• 65596-92-1 6-(4-nitrophenyl)-hexanoic acid 
• 1135871-94-1 N-(6-phenyl-hexanoyl)-6-(8-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-pyridine-2-sulfonamide 

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A photoinduced carboxylation of alkyl halides with CO2 at remote sp3 C?H sites enabled by the merger of photoredox and Ni catalysis is described. This protocol features a predictable reactivity and site selectivity that can be modulated by the ligand backbone. Preliminary studies reinforce a rationale based on a dynamic displacement of the catalyst throughout the alkyl side chain.

Synthetic Applications and Mechanistic Studies of the Hydroxide-Mediated Cleavage of Carbon-Carbon Bonds in Ketones

The hydroxide-mediated cleavage of ketones into alkanes and carboxylic acids has been reinvestigated and the substrate scope extended to benzyl carbonyl compounds. The transformation is performed with a 0.05 M ketone solution in refluxing xylene in the presence of 10 equiv of potassium hydroxide. The reaction constitutes a straightforward protocol for the synthesis of certain phenyl-substituted carboxylic acids from 2-phenylcycloalkanones. The mechanism was investigated by kinetic experiments which indicated a first order reaction in hydroxide and a full negative charge in the rate-determining step. The studies were complemented by a theoretical investigation where two possible pathways were characterized by DFT/M06-2X. The calculations showed that the scission takes place by nucleophilic attack of hydroxide on the ketone followed by fragmentation of the resulting oxyanion into the carboxylic acid and a benzyl anion.