6005-99-8

Usage

Uses

Used in Fragrance Industry:
N-Tridecanophenone is used as a fragrance ingredient for its distinctive odor. It contributes to the creation of various scent profiles in perfumes, colognes, and other fragranced products.
Used in Flavor Industry:
As a flavoring agent, N-Tridecanophenone enhances the taste of food and beverages, providing a unique flavor profile that can be tailored to specific applications.
Used in Pharmaceutical Industry:
N-Tridecanophenone serves as an intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of new drugs and medications.
Used in Cosmetic and Personal Care Industry:
N-TRIDECANOPHENONE is used as an ingredient in a wide range of cosmetic and personal care products, such as creams, lotions, and shampoos, due to its ability to improve the texture and consistency of these formulations.
Used as a Plasticizer:
N-Tridecanophenone is utilized as a plasticizer to increase the flexibility and workability of various types of plastics, making them more suitable for specific applications.

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 
• 17746-06-4 n-tridecanoyl chloride 
• 71-43-2 benzene 
• 1851-92-9 1-hydroxytridecylbenzene 
• 77815-56-6 Trimethyl-(1-phenyl-1-phenylsulfanyl-tridecyloxy)-silane 
• 112-41-4 1-dodecene 
• 98-88-4 benzoyl chloride 
• 4292-19-7 1-Iodododecane 
• 143-15-7 1-dodecylbromide 
• 22986-80-7 2-hydroxy-2-phenyltetradecanoic acid 
• 611-71-2 MANDELIC ACID 
• 6337-34-4 2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one 
• 830341-88-3 5-dodecyl-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one 

Downstream Products

• 124573-35-9 2-Phenyl-1-tetradecene 
• 132362-82-4 (S)-1-phenyl-1-tridecanol 
• 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 
• 4534-59-2 1-methyltridecylbenzene 
• 94681-69-3 tetradec-2-en-2-ylbenzene 
• 51439-05-5 Benzyl-n-dodecylketon 

Relevant academic research and scientific papers

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.

METHOD FOR CONVERTING HYDROXYL GROUP OF ALCOHOL

The present invention relates to: a method for converting a hydroxyl group of an alcohol; and a catalyst which makes the method possible. A method for converting a hydroxyl group of an alcohol according to the present invention is characterized by producing a compound represented by CH(R1)(R2)Nu (wherein R1, R2 and Nu are as defined below) by reacting an alcohol represented by CH(R1)(R2)OH (wherein each of R1 and R2 represents a hydrogen atom, an optionally substituted alkyl group, or the like) and a compound having an active proton, which is represented by H-Nu (wherein Nu represents a group represented by —CHX1-EWG1 or —NR3R4; X1 represents a hydrogen atom or the like; EWG1 represents an electron-withdrawing group; and each of R3 and R4 represents a hydrogen atom, an optionally substituted alkyl group, or the like), with each other in the presence of a complex of a group 7-11 metal of the periodic table and at least one solid base that is selected from the group consisting of layered double hydroxides, composite oxides and calcium hydroxide.

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.

Solvent-free direct α-alkylation of ketones by alcohols catalyzed by nickel supported on silica-alumina

The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis. Ni/SiO2-Al2O3 was found to be the best catalyst for this transformation and the corresponding alkylated acetophenone was obtained with 93% isolated yield. Following the objectives of clean and sustainable chemistry, the reaction occurs under solvent-free conditions and requires only a catalytic amount of base. This protocol was next applied to a wide range of ketones and alcohols and the desired products were isolated with 18-86% yields (26 examples). The recovery and recyclability of the nickel catalyst was also investigated and it was found to be active over 5 runs without significant loss of activity. Surprisingly, the active catalyst appears to include an amorphous nickel hydroxide layer.

Method for directly oxidizing benzyl-position C-H bond into ketone

The invention discloses a method for directly oxidizing a benzyl-position C-H bond into ketone, wherein aryl ethyl compounds are catalyzed and oxidized by nitrite ester; a synergistic catalytic system of free radical initiator and nitrite ester is adopted, and a catalytic system of non-metallic catalyst and oxygen is adopted, the oxidization of the C-H bond of a free radical-activated aryl side chain is simple in operation; after completing the reaction, petroleum ether/ethyl acetate at a volume ratio of (50-1):1 is used as an eluent; column chromatography separation is performed to obtain a target product. The catalytic system in the invention uses oxygen as an oxygen source and has high atomic economy; the invention is a non-metallic catalytic system and provides a novel method for avoid metal residues in synthetic drugs; for diethyl aromatic hydrocarbon, the method provided by the invention can be adopted to selectively oxidize diethyl aromatic hydrocarbon into monoketone and diketone; the method of the invention can be adopted to efficiently synthesize tranquillizer lenperone, so that a novel method for synthesizing lenperone is provided.

Iron-Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides

An iron-catalyzed oxyalkylation of alkynes with alkyl peroxides as the alkylating reagents has been investigated. Alkyl peroxides are readily available from aliphatic acids and serve simultaneously as the alkylating reagents and internal oxidants. Primary, secondary, and tertiary alkyl groups of aliphatic acids were readily incorporated into C?C triple bonds and diverse α-alkylated ketones were synthesized. Mechanism studies revealed that this reaction involves highly reactive alkyl free radicals. A unique equilibrium between lauric acid and water catalyzed by the iron(III) catalyst was observed.

Synthesis of new chiral and racemic 1,3-dioxolanes

A series of chiral 1,3-dioxolanes, 3-12, with >99% ee values, have been synthesized. This is the first study of chiral ketalization reaction starting from ketones with aryl, monosubstituted aryl, and long alkyl chains (C 11-AC13). Their ee values were determined by chiral high-performance liquid chromatography (HPLC) on Chiralcel OD column, using their racemic 1,3-dioxolanes rac-3-12, which were also synthesized for the first time. These chiral and racemic 1,3-dioxolanes were characterizated by infrared, NMR (1H, 13C), mass spectrometry, elemental analysis, optical rotation, and chiral HPLC.

Synthesis of new chiral and racemic 1,3-dioxolanes

A series of chiral 1,3-dioxolanes, 3-12, with >99% ee values, have been synthesized. This is the first study of chiral ketalization reaction starting from ketones with aryl, monosubstituted aryl, and long alkyl chains (C 11-AC13). Their ee values were determined by chiral high-performance liquid chromatography (HPLC) on Chiralcel OD column, using their racemic 1,3-dioxolanes rac-3-12, which were also synthesized for the first time. These chiral and racemic 1,3-dioxolanes were characterizated by infrared, NMR (1H, 13C), mass spectrometry, elemental analysis, optical rotation, and chiral HPLC.

Synthesis, insecticidal evaluation of novel 1,3,4-thiadiazole chrysanthemamide derivatives formed by an EDCI/HOBt condensation

A series of novel pesticides with two components derived from a 1,3,4-thiadiazole and chrysanthemic acid were synthesised via an EDCI/HOBt condensation. These 1,3,4-thiadiazole chrysanthemamides were identified by IR, 1H NMR and elemental analyses. Their insecticidal activity was also evaluated.