6005-99-8

Basic information

• Product Name: N-TRIDECANOPHENONE
• Synonyms: N-DODECYL PHENYL KETONE;N-TRIDECANOPHENONE;Tridecanophenone;Dodecyl Phenyl Ketone;1-Phenyl-1-tridecanone;1-Phenyltridecane-1-one
• CAS NO: 6005-99-8
• Molecular Formula: C₁₉H₃₀O
• Molecular Weight: 274.44
• Mol File: 6005-99-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 42 °C
• Boiling Point: 374.5 °C at 760 mmHg
• Flash Point: 142 °C
• Appearance: /
• Density: 0.907g/cm³
• CAS DataBase Reference: N-TRIDECANOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: N-TRIDECANOPHENONE(6005-99-8)
• EPA Substance Registry System: N-TRIDECANOPHENONE(6005-99-8)

Safety Data

• Hazardous Substances Data: 6005-99-8(Hazardous Substances Data)

Usage

General Description

N-Tridecanophenone, also known as 1-(tridecyl)phenylketone, is an organic compound belonging to the class of ketones. It is a colorless to pale yellow liquid with a distinctive odor. N-Tridecanophenone is commonly used in the manufacturing of fragrances, as a flavoring agent, and as an intermediate in the synthesis of pharmaceuticals and other organic compounds. It is also used as a plasticizer and as an ingredient in various cosmetic and personal care products. N-Tridecanophenone is considered to have low toxicity and is not expected to cause any harmful effects under normal handling and use.

Synthetic route

(tridec-1-ynyl)benzene → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; trifluorormethanesulfonic acid In tetrahydrofuran at 100℃; for 12h; Schlenk technique; Inert atmosphere;	98%

C31H52O2 → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; trifluorormethanesulfonic acid In tetrahydrofuran at 100℃; for 12h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	96%

2-hydroxy-2-phenyltetradecanoic acid (22986-80-7) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)); oxygen; pivalaldehyde In acetonitrile for 2h; Ambient temperature;	95%
With (NMe4)Co(III)Me2opba*2H2O*CH3CN; oxygen; pivalaldehyde In acetonitrile for 2h;	95%
With oxygen; pivalaldehyde; Co(III) ortho-phenylene-bis(N'-methyloxamidate) In acetonitrile at 20℃;	95%

1-dodecene (112-41-4) + 3-phenyl-propenal → tetradecan-2-one (2345-27-9) + 1-phenyltridecan-1-one

Conditions	Yield
Stage #1: 1-dodecene; 3-phenyl-propenal With 3-methylpyridin-2-ylamine; Wilkinson's catalyst; 4-trifluoromethylbenzoic acid; cyclohexylamine In toluene at 130℃; for 12h; Stage #2: With hydrogenchloride; water In tetrahydrofuran	A 92% B 91%

1-dodecene + benzaldehyde (100-52-7) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With dipotassium peroxodisulfate; methylene blue; potassium carbonate In water at 25℃; for 12h; Irradiation; Green chemistry;	82%

1-dodecyl alcohol (112-53-8) + acetophenone (98-86-2) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With Mg-Al hydrotalcite; chloro[N-[4-(dimethylamino)phenyl]-2-pyridinecarboxamidato](pentamethylcyclopentadienyl)iridium In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 8h; Schlenk technique;	80%

dilauryl peroxide (105-74-8) + phenylacetylene (536-74-3) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; trifluorormethanesulfonic acid In tetrahydrofuran at 60 - 100℃; for 13h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;	78%

tridecylbenzene (123-02-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With tert.-butylnitrite; N-hydroxyphthalimide In acetonitrile at 80℃; for 24h; Schlenk technique;	70%

benzoyl chloride (98-88-4) + 1-dodecylbromide (143-15-7) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With manganese; ethylene dibromide In tetrahydrofuran Product distribution; 1.) 0 deg C to rt, 1 h; 2.) 0 deg C, 20 min; 3.) rt, 30 min; coupling of benzoyl chloride with organomanganese bromides;	68%
With manganese; ethylene dibromide In tetrahydrofuran 1.) 0 deg C to rt, 1 h; 2.) 0 deg C, 20 min; 3.) rt, 30 min;	68%

1-hydroxytridecylbenzene (1851-92-9, 132362-82-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With thio-xanthene-9-one In dimethyl sulfoxide for 18h; Irradiation; Green chemistry; chemoselective reaction;	66%
at 30℃; for 48h; by Corynebacterium equi IFO 3730;	91 % Chromat.

1-dodecene (112-41-4) + α-methyl-trans-cinnamaldehyde (15174-47-7) → pentadecan-3-one (18787-66-1) + 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Stage #1: 1-dodecene; α-methyl-trans-cinnamaldehyde With 3-methylpyridin-2-ylamine; Wilkinson's catalyst; 4-trifluoromethylbenzoic acid; cyclohexylamine In toluene at 130℃; for 12h; Stage #2: With hydrogenchloride; water In tetrahydrofuran	A 60% B 60%

2-methyl-1-phenylcyclododecanol → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
at 630℃; under 1.50012 Torr;	43%

10-Undecen-1-ol + acetophenone → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With potassium phosphate In neat (no solvent) at 175℃; for 24h; Sealed tube;	16%

laurylmagnesium bromide (15890-72-9) + benzonitrile (100-47-0) → 1-phenyltridecan-1-one (6005-99-8)

n-tridecanoyl chloride (17746-06-4) + benzene (71-43-2) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With aluminium trichloride
With aluminum (III) chloride for 3h; Friedel Crafts acylation; Reflux; Cooling with ice;
Friedel-Crafts Acylation;

Trimethyl-(1-phenyl-1-phenylsulfanyl-tridecyloxy)-silane (77815-56-6) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With aqueous acid Yield given;

1-dodecene (112-41-4) + benzoyl chloride (98-88-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With dichloroaluminum hydride; triethyl borane 1) 1,2-dichloroethane, RT, 1 h, 2) -25 deg C, 2 h; Yield given. Multistep reaction;

1-Iodododecane (4292-19-7) + benzoyl chloride (98-88-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With copper; zinc; tetrakis(triphenylphosphine) palladium(0) 1.) benzene, DMF, RT, 1h, 60 C, 3-4h; 2.) benzene, RT; Yield given. Multistep reaction;

MANDELIC ACID (611-71-2, 611-72-3, 17199-29-0, 90-64-2) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 65 percent / H2SO4 / toluene / 24 h / 20 °C 2.1: n-BuLi; iPr2NH / hexane; tetrahydrofuran / 0.5 h / -78 °C 2.2: 65 percent / HMPA / hexane; tetrahydrofuran / 4 h / -78 - 20 °C 3.1: 100 percent / KOH / ethanol / 2 h / 20 °C 4.1: 95 percent / pivalaldehyde; O2 / Co(III)-Me2opba / acetonitrile / 20 °C View Scheme

2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one (6337-34-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-BuLi; iPr2NH / hexane; tetrahydrofuran / 0.5 h / -78 °C 1.2: 65 percent / HMPA / hexane; tetrahydrofuran / 4 h / -78 - 20 °C 2.1: 100 percent / KOH / ethanol / 2 h / 20 °C 3.1: 95 percent / pivalaldehyde; O2 / Co(III)-Me2opba / acetonitrile / 20 °C View Scheme

5-dodecyl-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one (830341-88-3) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / KOH / ethanol / 2 h / 20 °C 2: 95 percent / pivalaldehyde; O2 / Co(III)-Me2opba / acetonitrile / 20 °C View Scheme

(RS)-methyl mandelate (4358-87-6) + XCH2CO2Me → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: LDA / tetrahydrofuran / -78 - 20 °C 2: KOH / ethanol / 20 °C 3: 95 percent / (NMe4)Co(III)Me2opba*2H2O*CH3CN; pivalaldehyde; O2 / acetonitrile / 2 h View Scheme

methyl 2-hydroxy-2-phenyltetradecanoate (334927-76-3) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / ethanol / 20 °C 2: 95 percent / (NMe4)Co(III)Me2opba*2H2O*CH3CN; pivalaldehyde; O2 / acetonitrile / 2 h View Scheme
Multi-step reaction with 2 steps 1: NaOH 2: 95 percent / O2, pivalaldehyde, (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)) / acetonitrile / 2 h / Ambient temperature View Scheme

1-Iodododecane (4292-19-7) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: LDA 2: NaOH 3: 95 percent / O2, pivalaldehyde, (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)) / acetonitrile / 2 h / Ambient temperature View Scheme

(RS)-methyl mandelate (4358-87-6) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: LDA 2: NaOH 3: 95 percent / O2, pivalaldehyde, (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)) / acetonitrile / 2 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: LDA 2: NaOH 3: 95 percent / O2, pivalaldehyde, (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)) / acetonitrile / 2 h / Ambient temperature View Scheme

1-dodecylbromide (143-15-7) + sodium-<5.6.7.8-tetrahydro-naphtholate-(1)> → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: LDA 2: NaOH 3: 95 percent / O2, pivalaldehyde, (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)) / acetonitrile / 2 h / Ambient temperature View Scheme

Benzyl phenyl sulfide (831-91-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1) n-butyllithium - N,N,N'N'-tetramethylethylenediamine / 1) THF, -78 deg C 2: n-butyllithium - N,N,N'N'-tetramethylethylenediamine complex / hexane, 0 deg C 3: m-chloroperbenzoic acid / CH2Cl2 4: benzene / Heating 5: aqueous acid View Scheme

trimethylsilane (67274-35-5, 321038-62-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: n-butyllithium - N,N,N'N'-tetramethylethylenediamine complex / hexane, 0 deg C 2: m-chloroperbenzoic acid / CH2Cl2 3: benzene / Heating 4: aqueous acid View Scheme

benzyl bromide (100-39-0) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: 95 percent / ethanol 2: 1) n-butyllithium - N,N,N'N'-tetramethylethylenediamine / 1) THF, -78 deg C 3: n-butyllithium - N,N,N'N'-tetramethylethylenediamine complex / hexane, 0 deg C 4: m-chloroperbenzoic acid / CH2Cl2 5: benzene / Heating 6: aqueous acid View Scheme

1-phenyl-1-phenylthio-1-trimethylsilyltridecane (77815-49-7) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: m-chloroperbenzoic acid / CH2Cl2 2: benzene / Heating 3: aqueous acid View Scheme

1-phenyltridecan-1-one (6005-99-8) → (S)-1-phenyl-1-tridecanol (132362-82-4)

Conditions	Yield
Stage #1: 1-phenyltridecan-1-one With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 0 - 20℃; for 1.66667h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene Inert atmosphere; optical yield given as %ee; enantioselective reaction;	96%

1-hydroxytridecylbenzene (1851-92-9, 132362-82-4) → 1-phenyltridecan-1-one

Conditions	Yield
With thio-xanthene-9-one In dimethyl sulfoxide for 18h; Irradiation; Green chemistry; chemoselective reaction;	66%
at 30℃; for 48h; by Corynebacterium equi IFO 3730;	91 % Chromat.

1-phenyltridecan-1-one (6005-99-8) → 1-hydroxytridecylbenzene (1851-92-9, 132362-82-4)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 5℃;

1-phenyltridecan-1-one (6005-99-8) → 1-phenyl-tridecan-1-one semicarbazone

1-phenyltridecan-1-one (6005-99-8) + ethyl bromoacetate (105-36-2) → 3-hydroxy-3-phenyl-pentadecanoic acid ethyl ester

Conditions	Yield
With zinc

(tridec-1-ynyl)benzene → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; trifluorormethanesulfonic acid In tetrahydrofuran at 100℃; for 12h; Schlenk technique; Inert atmosphere;	98%

C31H52O2 → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; trifluorormethanesulfonic acid In tetrahydrofuran at 100℃; for 12h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	96%

2-hydroxy-2-phenyltetradecanoic acid (22986-80-7) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)); oxygen; pivalaldehyde In acetonitrile for 2h; Ambient temperature;	95%
With (NMe4)Co(III)Me2opba*2H2O*CH3CN; oxygen; pivalaldehyde In acetonitrile for 2h;	95%
With oxygen; pivalaldehyde; Co(III) ortho-phenylene-bis(N'-methyloxamidate) In acetonitrile at 20℃;	95%

1-dodecene (112-41-4) + 3-phenyl-propenal (104-55-2) → tetradecan-2-one (2345-27-9) + 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Stage #1: 1-dodecene; 3-phenyl-propenal With 3-methylpyridin-2-ylamine; Wilkinson's catalyst; 4-trifluoromethylbenzoic acid; cyclohexylamine In toluene at 130℃; for 12h; Stage #2: With hydrogenchloride; water In tetrahydrofuran	A 92% B 91%

1-dodecene (112-41-4) + benzaldehyde (100-52-7) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With dipotassium peroxodisulfate; methylene blue; potassium carbonate In water at 25℃; for 12h; Irradiation; Green chemistry;	82%

1-dodecyl alcohol (112-53-8) + acetophenone (98-86-2) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With Mg-Al hydrotalcite; chloro[N-[4-(dimethylamino)phenyl]-2-pyridinecarboxamidato](pentamethylcyclopentadienyl)iridium In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 8h; Schlenk technique;	80%

dilauryl peroxide (105-74-8) + phenylacetylene (536-74-3) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; trifluorormethanesulfonic acid In tetrahydrofuran at 60 - 100℃; for 13h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;	78%

tridecylbenzene (123-02-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With tert.-butylnitrite; N-hydroxyphthalimide In acetonitrile at 80℃; for 24h; Schlenk technique;	70%

benzoyl chloride (98-88-4) + 1-dodecylbromide (143-15-7) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With manganese; ethylene dibromide In tetrahydrofuran Product distribution; 1.) 0 deg C to rt, 1 h; 2.) 0 deg C, 20 min; 3.) rt, 30 min; coupling of benzoyl chloride with organomanganese bromides;	68%
With manganese; ethylene dibromide In tetrahydrofuran 1.) 0 deg C to rt, 1 h; 2.) 0 deg C, 20 min; 3.) rt, 30 min;	68%

1-hydroxytridecylbenzene (1851-92-9, 132362-82-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With thio-xanthene-9-one In dimethyl sulfoxide for 18h; Irradiation; Green chemistry; chemoselective reaction;	66%
at 30℃; for 48h; by Corynebacterium equi IFO 3730;	91 % Chromat.

1-dodecene (112-41-4) + α-methyl-trans-cinnamaldehyde (15174-47-7) → pentadecan-3-one (18787-66-1) + 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Stage #1: 1-dodecene; α-methyl-trans-cinnamaldehyde With 3-methylpyridin-2-ylamine; Wilkinson's catalyst; 4-trifluoromethylbenzoic acid; cyclohexylamine In toluene at 130℃; for 12h; Stage #2: With hydrogenchloride; water In tetrahydrofuran	A 60% B 60%

2-methyl-1-phenylcyclododecanol → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
at 630℃; under 1.50012 Torr;	43%

10-Undecen-1-ol (112-43-6) + acetophenone (98-86-2) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With potassium phosphate In neat (no solvent) at 175℃; for 24h; Sealed tube;	16%

laurylmagnesium bromide (15890-72-9) + benzonitrile (100-47-0) → 1-phenyltridecan-1-one (6005-99-8)

n-tridecanoyl chloride (17746-06-4) + benzene (71-43-2) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With aluminium trichloride
With aluminum (III) chloride for 3h; Friedel Crafts acylation; Reflux; Cooling with ice;
Friedel-Crafts Acylation;

Trimethyl-(1-phenyl-1-phenylsulfanyl-tridecyloxy)-silane (77815-56-6) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With aqueous acid Yield given;

1-dodecene (112-41-4) + benzoyl chloride (98-88-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With dichloroaluminum hydride; triethyl borane 1) 1,2-dichloroethane, RT, 1 h, 2) -25 deg C, 2 h; Yield given. Multistep reaction;

1-Iodododecane (4292-19-7) + benzoyl chloride (98-88-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
With copper; zinc; tetrakis(triphenylphosphine) palladium(0) 1.) benzene, DMF, RT, 1h, 60 C, 3-4h; 2.) benzene, RT; Yield given. Multistep reaction;

MANDELIC ACID (611-71-2, 611-72-3, 17199-29-0, 90-64-2) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 65 percent / H2SO4 / toluene / 24 h / 20 °C 2.1: n-BuLi; iPr2NH / hexane; tetrahydrofuran / 0.5 h / -78 °C 2.2: 65 percent / HMPA / hexane; tetrahydrofuran / 4 h / -78 - 20 °C 3.1: 100 percent / KOH / ethanol / 2 h / 20 °C 4.1: 95 percent / pivalaldehyde; O2 / Co(III)-Me2opba / acetonitrile / 20 °C View Scheme

2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one (6337-34-4) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-BuLi; iPr2NH / hexane; tetrahydrofuran / 0.5 h / -78 °C 1.2: 65 percent / HMPA / hexane; tetrahydrofuran / 4 h / -78 - 20 °C 2.1: 100 percent / KOH / ethanol / 2 h / 20 °C 3.1: 95 percent / pivalaldehyde; O2 / Co(III)-Me2opba / acetonitrile / 20 °C View Scheme

5-dodecyl-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one (830341-88-3) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / KOH / ethanol / 2 h / 20 °C 2: 95 percent / pivalaldehyde; O2 / Co(III)-Me2opba / acetonitrile / 20 °C View Scheme

(RS)-methyl mandelate (4358-87-6) + XCH2CO2Me → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: LDA / tetrahydrofuran / -78 - 20 °C 2: KOH / ethanol / 20 °C 3: 95 percent / (NMe4)Co(III)Me2opba*2H2O*CH3CN; pivalaldehyde; O2 / acetonitrile / 2 h View Scheme

methyl 2-hydroxy-2-phenyltetradecanoate (334927-76-3) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / ethanol / 20 °C 2: 95 percent / (NMe4)Co(III)Me2opba*2H2O*CH3CN; pivalaldehyde; O2 / acetonitrile / 2 h View Scheme
Multi-step reaction with 2 steps 1: NaOH 2: 95 percent / O2, pivalaldehyde, (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)) / acetonitrile / 2 h / Ambient temperature View Scheme

1-Iodododecane (4292-19-7) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: LDA 2: NaOH 3: 95 percent / O2, pivalaldehyde, (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)) / acetonitrile / 2 h / Ambient temperature View Scheme

(RS)-methyl mandelate (4358-87-6) → 1-phenyltridecan-1-one (6005-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: LDA 2: NaOH 3: 95 percent / O2, pivalaldehyde, (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)) / acetonitrile / 2 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: LDA 2: NaOH 3: 95 percent / O2, pivalaldehyde, (NMe4)*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)) / acetonitrile / 2 h / Ambient temperature View Scheme

Upstream product

• 15890-72-9 laurylmagnesium bromide 
• 100-47-0 benzonitrile 
• 112-53-8 1-dodecyl alcohol 
• 98-86-2 acetophenone 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 112-43-6 10-Undecen-1-ol 
• 112-41-4 1-dodecene 
• 123-02-4 tridecylbenzene 
• 105-74-8 dilauryl peroxide 
• 536-74-3 phenylacetylene 
• 143-07-7 lauric acid 
• 638-53-9 tridecanoic acid 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 

Downstream Products

• 1851-92-9 1-hydroxytridecylbenzene 
• 1233091-82-1 5-(4-dodecylphenyl)-1,3,4-thiadiazol-2-amine 
• 1369885-82-4 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-N-(5-(4-dodecylphenyl)-1,3,4-thiadiazol-2-yl)-2,2-dimethylcyclopropanecarboxamide 
• 123-01-3 1-dodecylbenzene 
• 6313-88-8 4-dodecylacetophenone 
• 21021-55-6 4-dodecylbenzoic acid 
• 1411975-14-8 diisobutyl (4R,5R)-2-phenyl-2-dodecyl-1,3-dioxolane-4,5-dicarboxylate 
• 1411975-13-7 dimethyl (4R,5R)-2-phenyl-2-dodecyl-1,3-dioxolane-4,5-dicarboxylate 
• 132362-86-8 C₂₁H₃₄O₂ 
• 1271732-51-4 (R)-1-phenyl-1-tridecanol 
• 132362-82-4 (S)-1-phenyl-1-tridecanol 
• 4534-59-2 1-methyltridecylbenzene 
• 94681-69-3 tetradec-2-en-2-ylbenzene 
• 51439-05-5 Benzyl-n-dodecylketon 

Relevant articles and documents

Method for preparing aldehyde/ketone by breaking C-C key

The invention discloses a method for preparing aldehyde/ketone by breaking C-C bonds, and the method comprises the following steps of anaerobic condition. In an organic solvent system, an alcohol is used as a reaction raw material, and the C-C bond is selectively broken under the common action of an iron catalyst, an organic base and an additive to obtain aldehyde/ketone. The method is low in cost, easy to obtain, wide in substrate range, simple and product in post-treatment and high in purity, a new synthetic route and a method are developed for an aldehyde ketone compound, and the method has good application potential and research value.

Photochemical oxidation of benzylic primary and secondary alcohols utilizing air as the oxidant

A mild and green photochemical protocol for the oxidation of alcohols to aldehydes and ketones was developed. Utilizing thioxanthenone as the photocatalyst, molecular oxygen from air as the oxidant and cheap household lamps or sunlight as the light source, a variety of primary and secondary alcohols were converted into the corresponding aldehydes or ketones in low to excellent yields. The reaction mechanism was extensively studied.

Visible-Light-Driven Epoxyacylation and Hydroacylation of Olefins Using Methylene Blue/Persulfate System in Water

A visible-light-driven strategy for hydroacylation and epoxyacylation of olefins in water using methylene blue as photoredox catalyst and persulfate as oxidant is reported. In this unprecedented unified approach, two different transformations are accomplished using only one set of reagents. The method has a broad scope spanning a range of aromatic and aliphatic aldehydes as well as conjugated and nonconjugated olefins to deliver ketones and epoxyketones from abundant and inexpensive chemical feedstocks.