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1078-19-9 Usage

Chemical Properties

yellow to light brown fine crystalline powder

Uses

6-Methoxy-1-tetralone is a reagent useful in the synthesis of (2-(furanyl)vinyl)-1-tetralone chalcones which possesses anticancer agents and inducers of apoptosis.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 94, 1942 DOI: 10.1021/ja01253a025Tetrahedron Letters, 9, p. 2917, 1968 DOI: 10.1016/S0040-4039(00)89611-2

Synthesis

The synthesis of?6-methoxy-1-tetralone is as follows:Eaton's reagent (1.00 mL, 5.31 mmol) was added slowly to a stirred solution of methyl 4-(3-methoxyphenyl)butanoate (4; 0.37g, 1.78 mmol) in DCE (1 mL). The resulting mixture was stirred at 75 °C for 2h under N2 atmosphere. Then, the reaction mixture was allowed to reach room temperature, and was poured over ice-water and extracted with EtOAc (3 × 15 mL). The combined organic extracts were washed successively with brine (2 × 15 mL) and H2O (2 × 20 mL), filtered over Na2SO4 and concentrated under reduced pressure. The resulting brownish oil was fractionated by column chromatography (silica gel, EtOAc-hexanes, 1:9) to obtain 6-methoxy-1-tetralone as ayellowish oil; yield: 0.28 g (91%).

Check Digit Verification of cas no

The CAS Registry Mumber 1078-19-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 8 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1078-19:
(6*1)+(5*0)+(4*7)+(3*8)+(2*1)+(1*9)=69
69 % 10 = 9
So 1078-19-9 is a valid CAS Registry Number.
InChI:InChI=1/C11H12O2/c1-13-9-5-6-10-8(7-9)3-2-4-11(10)12/h5-7H,2-4H2,1H3

1078-19-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A15967)  6-Methoxy-1-tetralone, 99%   

  • 1078-19-9

  • 5g

  • 104.0CNY

  • Detail
  • Alfa Aesar

  • (A15967)  6-Methoxy-1-tetralone, 99%   

  • 1078-19-9

  • 25g

  • 369.0CNY

  • Detail
  • Alfa Aesar

  • (A15967)  6-Methoxy-1-tetralone, 99%   

  • 1078-19-9

  • 100g

  • 1066.0CNY

  • Detail

1078-19-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-Methoxytetralone

1.2 Other means of identification

Product number -
Other names 6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1078-19-9 SDS

1078-19-9Synthetic route

6-methoxy-3,4-dihydro-2H-spiro[naphthalene-1,2'-[1,3]dithiane]
180331-07-1

6-methoxy-3,4-dihydro-2H-spiro[naphthalene-1,2'-[1,3]dithiane]

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With periodic acid In tetrahydrofuran; diethyl ether for 0.1h; Ambient temperature;96%
Stage #1: 6-methoxy-3,4-dihydro-2H-spiro[naphthalene-1,2'-[1,3]dithiane] With chloro-trimethyl-silane; sodium iodide In acetonitrile at 20℃; for 24h;
Stage #2: With water In acetonitrile for 0.0833333h;
85%
6-methoxy-3,4-dihydro-2H-naphthalen-1-one-(2,4-dinitro-phenylhydrazone)
79128-80-6

6-methoxy-3,4-dihydro-2H-naphthalen-1-one-(2,4-dinitro-phenylhydrazone)

A

benzene-1,2,4-triamine
615-71-4

benzene-1,2,4-triamine

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With vanadium(II) chloride In tetrahydrofuran for 1h; Heating;A n/a
B 95%
4-(m-methoxyphenyl)-1,1,1-tris(phenylthio)butane
111171-80-3

4-(m-methoxyphenyl)-1,1,1-tris(phenylthio)butane

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In dichloromethane for 1h; Ambient temperature;95%
With DMTSF In dichloromethane for 0.25h; Product distribution; Ambient temperature; effect of various Lewis acids on cyclization followed hydrolyzis;78%
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; water; silver trifluoromethanesulfonate 1.) C6H6, 70 deg C, 1 h; 2.) CH3CN, 15 min; Yield given. Multistep reaction;
6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol
16821-32-2

6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide; Oxone; cetyltrimethylammonim bromide In water at 20℃; for 2h; Green chemistry; chemoselective reaction;95%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water at 25℃; for 24h; Micellar solution;93%
With diisopropyl-carbodiimide In toluene at 120℃; for 24h; Inert atmosphere; Sealed tube;92%
6'-methoxy-3',4'-dihydro-2'H-spiro[1,3-dithiolane-2,1'-naphthalene]
73622-41-0

6'-methoxy-3',4'-dihydro-2'H-spiro[1,3-dithiolane-2,1'-naphthalene]

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide In methanol; water Heating;95%
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 2h;65%
methyl 4-(3-methoxyphenyl)butanoate
57816-04-3

methyl 4-(3-methoxyphenyl)butanoate

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With Eaton’s reagent In 1,2-dichloro-ethane at 75℃; for 2h; Inert atmosphere;91%
C13H16O3

C13H16O3

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With lithium chloride In water; dimethyl sulfoxide at 90℃; for 6h;90%
6-methoxy-1-tetralone oxime
54951-36-9

6-methoxy-1-tetralone oxime

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With sodium bismuthate; water; silica gel for 0.05h;88%
With iodine; sodium dodecyl-sulfate In water at 25 - 40℃; for 4.5h;69.8%
6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With oxygen; 9,10-Dicyanoanthracene; Paraquat; iron(II) chloride In methanol; acetonitrile for 2h; Ambient temperature; Irradiation;87%
With tetrabutylammonium perchlorate; water; sodium acetate In acetonitrile Electrochemical reaction; Green chemistry;84.9%
With Bromotrichloromethane; Ir[2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine]2(4,4'-di-tert-butyl-2,2'-bipyridine)PF6; water; potassium carbonate In acetonitrile at 20℃; Irradiation; Inert atmosphere; regioselective reaction;78%
6-methoxy-1-(methoxymethylene)-1,2,3,4-tetrahydronaphthalene

6-methoxy-1-(methoxymethylene)-1,2,3,4-tetrahydronaphthalene

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper (II) carbonate hydroxide; TPGS-750-M In water at 20℃; Green chemistry;83%
methyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate
436155-55-4

methyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate

A

methyl (7-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)carbamate

methyl (7-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)carbamate

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
Stage #1: methyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃;
Stage #2: With boron trifluoride diethyl etherate In dichloromethane Further stages.;
A 82%
B 6%
4-(m-methoxyphenyl)-1,1,1-tris(methylthio)butane
129225-85-0

4-(m-methoxyphenyl)-1,1,1-tris(methylthio)butane

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In dichloromethane for 2h; Ambient temperature;78%
7-Methoxy-4-phenylsulfanyl-1,2-dihydro-naphthalene

7-Methoxy-4-phenylsulfanyl-1,2-dihydro-naphthalene

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With chloro-trimethyl-silane; water; sodium iodide; mercury dichloride In acetonitrile for 2h; Ambient temperature;77%
C13H16O2S

C13H16O2S

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With aluminium trichloride; potassium iodide In water; acetonitrile at 80℃; for 6h;77%
6-Methoxy-<1>tetralon-phenylhydrazon
6132-86-1

6-Methoxy-<1>tetralon-phenylhydrazon

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With hexamethylenetetramine; water for 0.0222222h; microwave irradiation;76%
6-methoxytetralone semicarbazone
57700-25-1

6-methoxytetralone semicarbazone

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With sodium bismuthate; silica gel for 0.133333h; Hydrolysis; microwave irradiation, solid phase reaction;73%
(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine
86770-53-8

(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine

A

4-iodo-7-methoxy-1,2-dihydronaphthalene
86770-56-1

4-iodo-7-methoxy-1,2-dihydronaphthalene

B

N,N'-Bis-[6-methoxy-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-hydrazine
86770-58-3

N,N'-Bis-[6-methoxy-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-hydrazine

C

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With tert-butyl-tetramethyl-guanidine; iodine In toluene for 0.25h; Product distribution; Ambient temperature; variation of solvent and base, optimize the yield of iodide;A 68%
B 15%
C 12%
6-methoxy-α-tetralone hydrazone
86770-53-8

6-methoxy-α-tetralone hydrazone

A

1,2-bis((E)-6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine
86770-58-3

1,2-bis((E)-6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine

B

4-iodo-7-methoxy-1,2-dihydronaphthalene
86770-56-1

4-iodo-7-methoxy-1,2-dihydronaphthalene

C

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; iodine In tetrahydrofuran at 20℃; for 0.5h;A 15%
B 68%
C 12%
With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; iodine In toluene at 20℃; for 0.5h;A 15%
B 68%
C 12%
Product distribution; effect of solvents (ether, THF, toluene, acetonitrile, DMF, DMSO);
6-Methoxy-1,2,3,4-tetrahydro-naphthalene-1-carbaldehyde
83390-26-5

6-Methoxy-1,2,3,4-tetrahydro-naphthalene-1-carbaldehyde

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water for 22h; Heating;67%
With alkaline tetrahydrofuran for 22h; Heating; Yield given;
(6-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol
114423-18-6

(6-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With molecular sieve; pyridinium chlorochromate In dichloromethane at 20℃; for 15h;67%
With dipyridinium dichromate; Celite In dichloromethane at 25℃; for 14h;60%
1-(4-methoxyphenyl)cyclobutan-1-ol
164171-80-6

1-(4-methoxyphenyl)cyclobutan-1-ol

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With dipotassium peroxodisulfate; silver nitrate In dichloromethane; water at 20℃; for 3h; Inert atmosphere; regioselective reaction;66%
With lithium perchlorate In acetonitrile at 0 - 20℃; for 3h; Electrochemical reaction; Sealed tube; Green chemistry; regioselective reaction;25%
1,3-dioxoisoindolin-2-yl 5-(4-methoxyphenyl)-5-oxopentanoate

1,3-dioxoisoindolin-2-yl 5-(4-methoxyphenyl)-5-oxopentanoate

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 7h; Irradiation;65%
6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

A

1,6-dimethoxy-tetralin
16821-24-2

1,6-dimethoxy-tetralin

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In methanol for 0.0833333h; Ambient temperature;A 19%
B 63%
6'-methoxy-3',4'-dihydrospiro<1,3-benzodithiole-2,1'(2'H)naphthalene>
87543-03-1

6'-methoxy-3',4'-dihydrospiro<1,3-benzodithiole-2,1'(2'H)naphthalene>

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; mercury(II) oxide In tetrahydrofuran; water62%
With tetrahydrofuran; mercury(II) oxide; boron trifluoride diethyl etherate62%
phenyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate
436155-56-5

phenyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate

A

phenyl (7-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)carbamate
436155-78-1

phenyl (7-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)carbamate

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
Stage #1: phenyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃;
Stage #2: With boron trifluoride diethyl etherate In dichloromethane Further stages.;
A 55%
B 4.7%
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

1-(4-methoxyphenyl)cyclobutan-1-ol
164171-80-6

1-(4-methoxyphenyl)cyclobutan-1-ol

A

1-(4-methoxyphenyl)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-butan-1-one

1-(4-methoxyphenyl)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-butan-1-one

B

1-(4-methoxyphenyl)-1-butanone
4160-51-4

1-(4-methoxyphenyl)-1-butanone

C

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With sodium persulfate; silver nitrate In water; dimethyl sulfoxide at 50℃; for 16h; Inert atmosphere;A 54%
B 7 mg
C 16%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

A

7-Methoxy-1-tetralone
6836-19-7

7-Methoxy-1-tetralone

B

6-methoxy-2,3-dihydronaphthalene-1,4-dione

6-methoxy-2,3-dihydronaphthalene-1,4-dione

C

1-tert-butylperoxy-6-methoxytetralin

1-tert-butylperoxy-6-methoxytetralin

D

1-tert-butylperoxy-7-methoxytetralin

1-tert-butylperoxy-7-methoxytetralin

E

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With copper(II) choride dihydrate; tetrabutyl-ammonium chloride; sodium carbonate; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 20℃; for 17h; Green chemistry;A 8%
B 12%
C n/a
D n/a
E 50%
6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

A

2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With dipotassium peroxodisulfate; copper(I) sulfate In water; acetonitrile at 65 - 70℃; for 3h;A 10%
B 45%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

A

7-methoxy-1,2,3,4-tetrahydro-1-naphthol
32820-10-3

7-methoxy-1,2,3,4-tetrahydro-1-naphthol

B

7-Methoxy-1-tetralone
6836-19-7

7-Methoxy-1-tetralone

C

6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol
16821-32-2

6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

D

1-tert-butylperoxy-6-methoxytetralin

1-tert-butylperoxy-6-methoxytetralin

E

1-tert-butylperoxy-7-methoxytetralin

1-tert-butylperoxy-7-methoxytetralin

F

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With copper(II) choride dihydrate; tetrabutyl-ammonium chloride; sodium carbonate; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 20℃; for 17h; Green chemistry;A n/a
B 17%
C n/a
D n/a
E n/a
F 39%
6-methoxy-1,2,3,4-tetrahydronaphthalene
1730-48-9

6-methoxy-1,2,3,4-tetrahydronaphthalene

A

7-Methoxy-1-tetralone
6836-19-7

7-Methoxy-1-tetralone

B

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; chromium(VI) oxide In dichloromethane for 9h; Ambient temperature;A 17%
B 36%
With tert.-butylhydroperoxide; bis-(tributyltin oxide) dioxochromium(VI) In dichloromethane at 40℃; for 7.5h;A 15%
B 32%
With tert.-butylhydroperoxide; 2,4-dimethyl-2,4-pentanediol cyclic Cr(VI) ester In tetrachloromethane; dichloromethane at 0℃; for 8h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With potassium permanganate; copper(II) sulfate In dichloromethane for 72h; Heating;A 5 % Chromat.
B 85 % Chromat.
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-methoxy-1-tetralone oxime
54951-36-9

6-methoxy-1-tetralone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride100%
With hydroxylamine hydrochloride; sodium acetate In methanol at 70℃; for 1.5h;96%
With hydroxylamine hydrochloride; sodium acetate In methanol; water at 60℃; for 12h;95%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol
16821-32-2

6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol for 4h;100%
With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Heating;99%
With methanol; sodium tetrahydroborate at 0 - 20℃;99%
methyl iodide
74-88-4

methyl iodide

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

2,2-dimethyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
21568-65-0

2,2-dimethyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one

Conditions
ConditionsYield
With sodium hydride In benzene Heating;100%
In benzene100%
With sodium hydride In benzene Heating / reflux;100%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-methoxy-1-(trimethylsilanyloxy)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile
80859-07-0

6-methoxy-1-(trimethylsilanyloxy)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile

Conditions
ConditionsYield
With zinc(II) chloride100%
With zinc(II) iodide for 48h; Ambient temperature;64%
With zinc(II) iodide In toluene; acetonitrile at 60℃; for 5h;56%
With zinc(II) iodide
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-methoxy-3,4-dihydronaphthalene-1-yl triflate
115375-59-2

6-methoxy-3,4-dihydronaphthalene-1-yl triflate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 40℃; for 24h; Solvent; Sealed tube; Inert atmosphere;100%
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With triethylamine In dichloromethane at 0℃; for 0.166667h;
Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0 - 20℃;
70%
With triethylamine In dichloromethane at 0℃; for 22h; Inert atmosphere; Reflux;69%
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane for 7h; Ambient temperature;62%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

2-chloro-6-methoxy-1-tetralone
35609-43-9

2-chloro-6-methoxy-1-tetralone

Conditions
ConditionsYield
With N-chloro-succinimide; thiourea In methanol at 23℃; for 0.333333h;100%
With 2,2,3,4,5,6-hexachloro-cyclohexa-2,4-dien-1-one In ethanol for 6h; Heating;71%
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: With p-toluenesulfonyl chloride In tetrahydrofuran at -78 - 20℃; for 1.33333h;
With N-chloro-succinimide; O,O-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) hydrazine-1,2-bis(carbothioate) In methanol at 25℃; for 0.666667h;99 %Chromat.
With 2,2,3,4,5,6-hexachloro-cyclohexa-2,4-dien-1-one In ethanol for 4h; Reflux;
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-methoxy-3,4-dihydronaphthalene-1-yl triflate
115375-59-2

6-methoxy-3,4-dihydronaphthalene-1-yl triflate

Conditions
ConditionsYield
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.75h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 0℃; for 3h;
100%
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere;89%
Stage #1: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
80%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(1R)-6-methoxy-1,2,3,4-tetrahydronaphthalene-1-ol

(1R)-6-methoxy-1,2,3,4-tetrahydronaphthalene-1-ol

Conditions
ConditionsYield
With formic acid; C38H40ClN2O2RhS; triethylamine In neat (no solvent) at 24 - 30℃; for 24h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;100%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C49H64FeNOP; hydrogen; sodium t-butanolate In isopropyl alcohol at 25 - 30℃; under 38002.6 Torr; for 12h; Autoclave; enantioselective reaction;99%
With C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 37503.8 Torr; for 16h; Glovebox; Autoclave; enantioselective reaction;99%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

[(6-methoxy-3,4-dihydro-1-naphthalenyl)oxy](dimethyl)-tert-butylsilane
582300-13-8

[(6-methoxy-3,4-dihydro-1-naphthalenyl)oxy](dimethyl)-tert-butylsilane

Conditions
ConditionsYield
With triethylamine; sodium iodide In acetonitrile at 20℃;100%
2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
72824-04-5

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

1-allyl-1,2,3,4-tetrahydro-6-methoxynaphthalen-1-ol
111221-68-2

1-allyl-1,2,3,4-tetrahydro-6-methoxynaphthalen-1-ol

Conditions
ConditionsYield
With methanol; indium (III) tris(hexamethyldisilyl) amide In toluene at 20℃; for 6h; Inert atmosphere;100%
With indium iodide In tetrahydrofuran at 40℃; for 24h;70%
N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(E)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one O-methyloxime

(E)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one O-methyloxime

Conditions
ConditionsYield
With sodium acetate In ethanol; water at 70℃; for 2h;100%
4-methoxybenzenesulfonyl hydrazide
1950-68-1

4-methoxybenzenesulfonyl hydrazide

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

4-methoxy-N'-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)benzenesulfonohydrazide

4-methoxy-N'-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)benzenesulfonohydrazide

Conditions
ConditionsYield
With acetic acid In ethanol Reflux;100%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-Hydroxy-1-tetralone
3470-50-6

6-Hydroxy-1-tetralone

Conditions
ConditionsYield
With hydrogen bromide for 3h; Heating;99%
With hydrogen bromide; acetic acid at 120℃; for 12h;98%
With aluminum (III) chloride In toluene for 1.08333h; Inert atmosphere; Sealed tube; Reflux;96%
Diethyl carbonate
105-58-8

Diethyl carbonate

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
16425-80-2

ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Conditions
ConditionsYield
Stage #1: Diethyl carbonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 6-methoxy-3,4-dihydro-1(2H)-naphthalenone In tetrahydrofuran; mineral oil at 0 - 80℃; for 12h; Inert atmosphere; Schlenk technique;
99%
With sodium hydride In tetrahydrofuran for 48h; Heating / reflux;91.8%
With sodium hydride85%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(1S)-6-methoxy-1,2,3,4-tetrahydronaphthalene-1-ol
16821-32-2, 42246-05-9, 120523-15-1

(1S)-6-methoxy-1,2,3,4-tetrahydronaphthalene-1-ol

Conditions
ConditionsYield
With Tetrahydrofurfuryl alcohol; sodium tetrahydroborate In ethanol; chloroform at -20℃; for 0.333333h;99%
With RuCl[(S)-daipena][(R)-dm-segphos]; potassium tert-butylate; hydrogen In ethanol; isopropyl alcohol at 15℃; under 7600.51 Torr; for 21h; optical yield given as %ee; enantioselective reaction;96%
With Tetrahydrofurfuryl alcohol; sodium tetrahydroborate; (1S,2S)-1,2-bis(3,5-dimethylphenyl)-N,N'-bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]ethylenediaminatocobalt(II) In methanol; chloroform at -30 - 10℃; for 9.75h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;96%
1,1-dimethylhydrazine
57-14-7

1,1-dimethylhydrazine

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

2-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)-1,1-dimethylhydrazine
16388-08-2

2-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)-1,1-dimethylhydrazine

Conditions
ConditionsYield
With acetic acid In benzene for 18h; Reflux;99%
With trifluoroacetic acid In benzene Reflux; Dean-Stark; Inert atmosphere;91%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine
86770-53-8

(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine

Conditions
ConditionsYield
With hydrazine In ethanol for 8h; Reflux;99%
4-Trifluoromethylbenzaldehyde
455-19-6

4-Trifluoromethylbenzaldehyde

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(E)-6-methoxy-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one

(E)-6-methoxy-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 4h;99%
tetrahydrogeraniol
106-21-8, 59204-02-3

tetrahydrogeraniol

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

C21H32O2

C21H32O2

Conditions
ConditionsYield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 1,3-bis((R)-1-(naphthalen-1-yl)ethyl)-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate; potassium tert-butylate; lithium tert-butoxide In hexane; pentan-1-ol at 100℃; for 24h;99%
5-methyl-indole-2,3-dione
608-05-9

5-methyl-indole-2,3-dione

3-amino-1-phenyl-2-pyrazolin-5-one
4149-06-8

3-amino-1-phenyl-2-pyrazolin-5-one

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

3-methoxy-5'-methyl-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

3-methoxy-5'-methyl-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

Conditions
ConditionsYield
With acetic acid In water at 90℃; for 7h; Green chemistry;99%
3-bromo-pyridine-4-carbaldehyde
70201-43-3

3-bromo-pyridine-4-carbaldehyde

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(E)-2-((3-bromopyridin-4-yl)methylene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one
1620646-31-2

(E)-2-((3-bromopyridin-4-yl)methylene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 35℃; for 4h;99%
formic acid ethyl ester
109-94-4

formic acid ethyl ester

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

2-(hydroxymethylene)-6-methoxy-1-tetralone
851486-82-3

2-(hydroxymethylene)-6-methoxy-1-tetralone

Conditions
ConditionsYield
With potassium tert-butylate In toluene at -78 - -5℃; for 1h;98%
With sodium methylate In pyridine for 18h; Ambient temperature;
formic acid ethyl ester
109-94-4

formic acid ethyl ester

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

6-Methoxy-2-hydroxymethylen-1-tetralon
16252-53-2

6-Methoxy-2-hydroxymethylen-1-tetralon

Conditions
ConditionsYield
With potassium tert-butylate In toluene at -78 - -5℃; Inert atmosphere;98%
Stage #1: formic acid ethyl ester; 6-methoxy-3,4-dihydro-1(2H)-naphthalenone With potassium tert-butylate at -78 - -5℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water
98%
With potassium tert-butylate In toluene at -78 - -5℃; Inert atmosphere;98%
methyllithium
917-54-4

methyllithium

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

1,2,3,4-tetrahydro-6-methoxy-1-methyl-1-naphthalenol
85035-85-4

1,2,3,4-tetrahydro-6-methoxy-1-methyl-1-naphthalenol

Conditions
ConditionsYield
With lithium bromide In tetrahydrofuran; diethyl ether Ambient temperature;98%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

methyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
40153-87-5

methyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Conditions
ConditionsYield
With sodium hydride Inert atmosphere; Reflux;98%
With sodium hydride Inert atmosphere; Reflux;98%
In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; acetic acid; mineral oil96%
3-amino-1-phenyl-2-pyrazolin-5-one
4149-06-8

3-amino-1-phenyl-2-pyrazolin-5-one

5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

5'-bromo-3-methoxy-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

5'-bromo-3-methoxy-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

Conditions
ConditionsYield
With acetic acid In water at 90℃; for 6h; Green chemistry;98%
3-Fluorobenzaldehyde
456-48-4

3-Fluorobenzaldehyde

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

(3-fluorobenzylidene)-6-methoxy-1-tetralone
304459-30-1

(3-fluorobenzylidene)-6-methoxy-1-tetralone

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 4h;97.8%
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

1,2,3,4-tetrahydro-6-methoxy-1-oxonaphthalen-2-yl acetate
66049-51-2

1,2,3,4-tetrahydro-6-methoxy-1-oxonaphthalen-2-yl acetate

Conditions
ConditionsYield
With acetic acid In benzene for 5h; Heating;97%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

urea
57-13-6

urea

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

4-(4-chlorophenyl)-3,4,5,6-tetrahydro-8-methoxybenzo[h]quinazolin-2-(1H)-one

4-(4-chlorophenyl)-3,4,5,6-tetrahydro-8-methoxybenzo[h]quinazolin-2-(1H)-one

Conditions
ConditionsYield
With (4-sulfobutyl)-tris(4-sulfophenyl)phosphonium hydrogen sulfate at 80℃; for 0.166667h;97%
7-chloroisatin
7477-63-6

7-chloroisatin

3-amino-1-phenyl-2-pyrazolin-5-one
4149-06-8

3-amino-1-phenyl-2-pyrazolin-5-one

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

7'-chloro-3-methoxy-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

7'-chloro-3-methoxy-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

Conditions
ConditionsYield
With acetic acid In water at 90℃; for 6h; Green chemistry;97%

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1078-19-9Relevant articles and documents

A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion

Yu, Jiajia,Zhao, Huijun,Liang, Shuguang,Bao, Xiaoguang,Zhu, Chen

, p. 7924 - 7927 (2015)

A regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion is described. A variety of 1-tetralones are furnished under mild reaction conditions from tertiary cyclobutanols regardless of the electronic properties and steric hindrance of substituents, providing a new and practical method to access diverse 1-tetralone building blocks. Preliminary experimental and DFT studies revealed that a radical-mediated sequence of C-C bond cleavage/C-C bond formation is involved.

1,3-BENZODITHIOLIUM ION MEDIATED ANNULATIONS

Rigby, James H.,Kotnis, Atul,Kramer, James

, p. 2939 - 2940 (1983)

A mild and selective method for cyclizations onto aromatic systems using 1,3-benzodithiolium ions is described.

AN IMPROVED PREPARATION OF VINYL IODIDES

Barton, Derek H. R.,Bashiardes, George,Fourrey, Jean-Louis

, p. 1605 - 1608 (1983)

The oxidation of ketone hydrazones by iodine in the presence of a base to furnish vinyl iodides has been considerably improved.The three factors responsible are (1) absence of water, (2) the use of strong guanidine bases and (3) inverse addition.

Chemoselective oxidation of benzylic alcohols with solid supported CrO3/TBHP under microwave irradiation

Singh,Sharma,Chhibber,Kaur,Kad

, p. 3941 - 3945 (2000)

The efficient use of microwave energy coupled with dry media technique for the oxidation of benzylic alcohols using catalytic CrO3 and TBHP has been effectively projected.

-

Juday

, p. 532,534 (1957)

-

PRACTICAL CHROMIUMVI OXIDE-CATALYZED BENZYLIC OXIDATIONS USING 70percent TERT-BUTYLHYDROPEROXIDE

Muzart, Jacques

, p. 2131 - 2132 (1987)

In using 70percent t.BuOOH and catalytic amounts of chromic anhydride, benzylic methylene groups are oxidized at room temperature to carbonyl functions in fair yields.

Birch et al.

, p. 2917 (1968)

Mechanical metal activation for Ni-catalyzed, Mn-mediated cross-electrophile coupling between aryl and alkyl bromides

Wu, Sisi,Shi, Weijia,Zou, Gang

supporting information, p. 11269 - 11274 (2021/07/02)

Liquid-assisted grinding has been successfully applied to eliminate the requirements of chemical activators and anhydrous solvents in nickel-catalyzed, manganese-mediated cross-electrophile coupling between aryl and alkyl bromides. In addition to the traditional reaction parameters, mechanical ones,e.g.the rotational speed of mill, the filling degree of jar and ball size, have been found to affect the catalytic efficiency remarkably, implying the involvement of the regeneration of nickel(0) species in the rate-determining steps. A combined evaluation of the reaction and mechanical parameters led to an optimal condition under which a variety ofn-alky aromatics with various functional groups could be readily obtained in good yields with a 1 mol% catalyst loading. The practical application of liquid-assisted grinding-enabled aryl/alkyl cross-electrophile coupling has been demonstrated in the gram-scale synthesis of 6-methoxytetralone.

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

Li, Zhibin,Zhang, Yan,Li, Kuiliang,Zhou, Zhenghong,Zha, Zhenggen,Wang, Zhiyong

, p. 2134 - 2141 (2021/09/29)

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

Highly selective electrocatalytic oxidation of benzyl C-H using water as safe and sustainable oxygen source

Ding, Mengning,Li, Xiaoshan,Sun, Yuxia,Xie, Jin,Xu, Wentao,Yang, Miao

supporting information, p. 7543 - 7551 (2020/11/18)

The selective oxidation of C-H bond is critical for feedstock manufacturing in chemical industry. Current strategies typically involve the use of oxygen or peroxide as the oxidation reagent under high temperature, which sets severe challenges in production sustainability and industrial safety. Herein, we demonstrate an environmental-friendly and safe electrocatalytic strategy for the selective oxidation of benzyl group to ketones at ambient conditions, while using water as the sole oxygen source. Water addition reduces the onset potential of anodic C-H oxidation, and produces 1-tetralone with satisfying conversion and excellent ketone to alcohol ratio. Layered MnO2 catalysts (with rich oxygen vacancies) further adjust the water affinity and facilitate the oxidation, leading to a significantly improved faradaic efficiency. This journal is

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