6836-19-7

Basic information

• Product Name: 7-Methoxy-1-tetralone
• Synonyms: 7-Methoxy-1,2,3,4-tetrahydronaphthalene-1-one;7-Methoxy-1-oxotetraline;7-Methoxy-1-tetralinone;7-Methoxy-1-tetralone,97%;7-M;7-methoxytetralin-1-one;3,4-Dihydro-7-methoxy-1(2H)-naphthalenone;7-Methoxy-1-tetralon
• CAS NO: 6836-19-7
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• EINECS: 229-916-0
• Product Categories: intermediates;Benzocycles;Naphthalene derivatives;Aromatics Compounds;Butorphanol;Aromatics;C11 to C12;Carbonyl Compounds;Ketones
• Mol File: 6836-19-7.mol
• Article Data: 45

Chemical Properties

• Melting Point: 59-63 °C(lit.)
• Boiling Point: 160-165 C
• Flash Point: 145.8 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.124 g/cm³
• Vapor Pressure: 0.000535mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility: 309mg/L at 25℃
• BRN: 2208389
• CAS DataBase Reference: 7-Methoxy-1-tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Methoxy-1-tetralone(6836-19-7)
• EPA Substance Registry System: 7-Methoxy-1-tetralone(6836-19-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 6836-19-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Powder

Uses

7-methoxy-1-tetralone was used in the synthesis of 2,7-dimethoxy-1-tetralone, substituted derivatives of 3a,4,5,6-tetrahydrosuccinimido[3,4-b]acenaphthen-10-one and 13H-benzo[6-7]indolo[3,2-c]quinolines.

InChI:InChI=1/C11H12O2/c1-13-9-6-5-8-3-2-4-11(12)10(8)7-9/h5-7H,2-4H2,1H3

Synthetic route

4-(4-methoxyphenyl) butanoyl chloride (6836-18-6) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
With Fe-Al-MCM-41 molecular sieve In toluene at 60℃; for 18h; Green chemistry;	98.4%
unter vermindertem Druck;
With aluminium trichloride; 1,1,2,2-tetrachloroethane at -5℃;

7-methoxy-1,2,3,4-tetrahydro-1-naphthol (32820-10-3) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
With acetone In toluene at 80℃; for 0.25h; Flow reactor;	96%

4-(4-Methoxyphenyl)butyric acid (4521-28-2) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
With phosphoric acid; phosphorus pentoxide at 70 - 80℃; for 2h;	94%
With trifluoroacetic anhydride In 1,2-dichloro-ethane at 0 - 20℃; Friedel-Crafts acylation;	94%
With trichloroacetic acid anhydride at 70℃; Friedel Crafts acylation; Neat (no solvent);	92%

(7-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol (106336-27-0) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
With dipyridinium dichromate; Celite In dichloromethane at 25℃; for 24h;	79%

dimethyl 1,2-dihydro-4-hydroxy-6-methoxynaphthalene-1,3-dicarboxylate (666177-27-1) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
With sodium chloride In dimethyl sulfoxide at 200℃;	65%

4-(4-Methoxy-phenyl)-butyryl azide → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
	64%

7-methoxy-8a-methyl-1,2,3,4,6,8a-hexahydro-naphthalen-1-one (65128-90-7) → 7-Methoxy-1-tetralone (6836-19-7) + (6S,8aS)-6-Hydroxy-7-methoxy-8a-methyl-3,4,6,8a-tetrahydro-2H-naphthalen-1-one + (6R,8aS)-6-Hydroxy-7-methoxy-8a-methyl-3,4,6,8a-tetrahydro-2H-naphthalen-1-one

Conditions	Yield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 4℃; pH=8.3;	A 63% B 20% C 12%

1,1-(1,2-Benzenediyldithio)-7-methoxy-1,2,3,4-tetrahydronaphthalene (87543-05-3) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
With boron trifluoride diethyl etherate; mercury(II) oxide In tetrahydrofuran; water	62%
With tetrahydrofuran; mercury(II) oxide; boron trifluoride diethyl etherate	56%

1-(3-methoxyphenyl)cyclobutan-1-ol (1202643-83-1) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
With potassium carbonate; copper(II) sulfate; Selectfluor In water; acetonitrile at 60℃; for 5h;	59%

8a-allyl-7-methoxy-1,2,3,4,6,8a-hexahydro-naphthalen-1-one (310897-19-9) → 7-Methoxy-1-tetralone (6836-19-7) + (6S,8aS)-8a-Allyl-6-hydroxy-7-methoxy-3,4,6,8a-tetrahydro-2H-naphthalen-1-one + (6R,8aS)-8a-Allyl-6-hydroxy-7-methoxy-3,4,6,8a-tetrahydro-2H-naphthalen-1-one

Conditions	Yield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 4℃; pH=8.3;	A 54% B 22.5% C 12.5%

tert.-butylhydroperoxide (75-91-2) + 6-methoxy-1,2,3,4-tetrahydronaphthalene (1730-48-9) → 7-Methoxy-1-tetralone (6836-19-7) + 6-methoxy-2,3-dihydronaphthalene-1,4-dione + 1-tert-butylperoxy-6-methoxytetralin + 1-tert-butylperoxy-7-methoxytetralin + 6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9)

Conditions	Yield
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%

7-methoxy-1,2,3,4-tetrahydro-1-naphthol (32820-10-3) → 7-Methoxy-1-tetralone (6836-19-7) + (+)-(S)-7-Methoxy-1-tetralol (182965-69-1) + (-)-(R)-7-Methoxy-1-tetralol

Conditions	Yield
With 4-vinylbenzyl chloride; [N,N'-bis(2-cyclohexyloxycarbonyl-3-oxobutylidene)-(1S,2S)-dimesitylethylenediaminato]cobalt(II); oxygen In tert-butyl alcohol at 20 - 50℃; for 12h; Resolution of racemate; optical yield given as %ee;	A 41.9% B n/a C n/a

tert.-butylhydroperoxide (75-91-2) + 6-methoxy-1,2,3,4-tetrahydronaphthalene (1730-48-9) → 7-methoxy-1,2,3,4-tetrahydro-1-naphthol (32820-10-3) + 7-Methoxy-1-tetralone (6836-19-7) + 6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol (16821-32-2) + 1-tert-butylperoxy-6-methoxytetralin + 1-tert-butylperoxy-7-methoxytetralin + 6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9)

Conditions	Yield
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) → 7-Methoxy-1-tetralone (6836-19-7) + 6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9)

Conditions	Yield
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-1,2,3,4-tetrahydronaphthalene (1730-48-9) → 7-Methoxy-1-tetralone (6836-19-7) + 6-methoxy-2,3-dihydronaphthalene-1,4-dione + 6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9)

Conditions	Yield
With tert.-butylhydroperoxide; sodium hydrogencarbonate; dirhodium(II) tetrakis(caprolactam) In decane; 1,2-dichloro-ethane at 20℃; for 16h; Title compound not separated from byproducts;	A n/a B 29% C n/a

7-hydroxy-1-tetralone (22009-38-7) + dimethyl sulfate (77-78-1) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
With potassium carbonate In acetone for 2.5h; Heating; Yield given;

dimethyl sulfate (77-78-1) + 7-hydroxy-1-oxo-tetralin → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
With sodium hydroxide

7-methoxy-3,4-dihydro-2H-<1-14C>naphthalen-1-one → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Herstellung;

methoxybenzene (100-66-3) + (+-)-propylsuccinic acid-anhydride → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 73.4 percent / AlCl3 / nitromethane / 12 h / 0 - 25 °C 2: 95 percent / NH2NH2*H2O; KOH / bis-(2-hydroxy-ethyl) ether / 7 h / 130 - 195 °C 3: 87.7 percent / H3PO4; P2O5 / 3 h / 70 - 80 °C View Scheme
Multi-step reaction with 3 steps 1: Zn; HCl / toluene 2: PPA View Scheme

4-(4-methoxy-phenyl)-4-oxo-butyric acid (3153-44-4) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / NH2NH2*H2O; KOH / bis-(2-hydroxy-ethyl) ether / 7 h / 130 - 195 °C 2: 87.7 percent / H3PO4; P2O5 / 3 h / 70 - 80 °C View Scheme
Multi-step reaction with 2 steps 1: Zn; HCl / toluene 2: PPA View Scheme
Multi-step reaction with 2 steps 1: Zn/HCl 2: CF3COOH, (CF3COO)2O View Scheme

4-(4-methoxyphenyl)-3-butenoic acid (91142-97-1) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / Pd/C / tetrahydrofuran / 3 h / 20 °C / 760.21 Torr 2: 94 percent / trifluoroacetic anhydride / 1,2-dichloro-ethane / 0 - 20 °C View Scheme

C23H38O3Sn → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrochloric acid / H2O / 0.25 h / 20 °C 2: hydrogen / Pd/C / tetrahydrofuran / 3 h / 20 °C / 760.21 Torr 3: 94 percent / trifluoroacetic anhydride / 1,2-dichloro-ethane / 0 - 20 °C View Scheme

methoxybenzene (100-66-3) + (+-)-hept-2t(?)-en-4-ol → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: AlCl3 2: Zn/HCl 3: CF3COOH, (CF3COO)2O View Scheme

methoxybenzene (100-66-3) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: 85 percent / polyphosphoric acid / 90 °C View Scheme
Multi-step reaction with 3 steps 1: 72 percent / AlCl3 / nitrobenzene / Ambient temperature 2: 87 percent / Zn, conc. HCl, HgCl2 / H2O; toluene / 24 h / Heating 3: 94 percent / P2O5, H3PO4 / 2 h / 70 - 80 °C View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / nitrobenzene / 0.5 h / 20 °C 1.2: 60 °C 2.1: palladium 10% on activated carbon; hydrogen / acetic acid / 70 °C 3.1: polyphosphoric acid / 90 °C View Scheme

1-<4,4-(1,2-Benzenediyldithio)but-3-enyl>-4-methoxybenzene (87543-11-1) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / p-toluenesulfonic acid / acetonitrile / 24 h / 0 °C 2: 56 percent / HgO, aq. THF / BF3.Et2O View Scheme
Multi-step reaction with 2 steps 1: 74 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 40 - 50 °C 2: 62 percent / mercury(II) oxide, BF3*Et2O / tetrahydrofuran; H2O View Scheme

7-Oxa-bicyclo[4.1.0]heptan-2-one oxime (58008-75-6) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / NaHCO3, CF3CO3H, urea / acetonitrile / 1.42 h / 0 °C 2: 85 percent / pyridinium chlorochromate / CH2Cl2 / 3.2 h / 23 °C 3: toluene / 19 h / 80 °C 4: 1.) hydrochloric acid 2.)DBN / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h 5: K2CO3 / acetone / 2.5 h / Heating View Scheme

3-nitro-2-cyclopenten-1-one (77970-17-3) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene / 19 h / 80 °C 2: 1.) hydrochloric acid 2.)DBN / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h 3: K2CO3 / acetone / 2.5 h / Heating View Scheme

3-nitro-2-cyclohexen-1-ol (67730-57-8) → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / pyridinium chlorochromate / CH2Cl2 / 3.2 h / 23 °C 2: toluene / 19 h / 80 °C 3: 1.) hydrochloric acid 2.)DBN / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h 4: K2CO3 / acetone / 2.5 h / Heating View Scheme

5-Methoxy-4a-nitro-7-trimethylsilanyloxy-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one → 7-Methoxy-1-tetralone (6836-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) hydrochloric acid 2.)DBN / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 1 h 2: K2CO3 / acetone / 2.5 h / Heating View Scheme

7-Methoxy-1-tetralone (6836-19-7) → 7-methoxy-3,4-dihydronaphthalen-1(2H)-one oxime (20175-97-7)

Conditions	Yield
With hydroxylamine hydrochloride; potassium carbonate In methanol for 16h; Reflux;	100%
With pyridine; hydroxylamine hydrochloride at 25℃; for 3h; Inert atmosphere;	94%
With hydroxylamine hydrochloride; potassium carbonate In methanol; water for 3h; Heating;	92%

diethyl 1-cyanomethylphosphonate (2537-48-6) + 7-Methoxy-1-tetralone (6836-19-7) → (7-methoxy-3,4-dihydro-2H-naphthalene-1-ylidene)acetonitrile (127299-26-7)

Conditions	Yield
With sodium methylate In methanol at -20 - -10℃; for 24h; Reagent/catalyst; Wittig Rearrangement;	100%
Stage #1: diethyl 1-cyanomethylphosphonate With potassium hydroxide In dimethyl sulfoxide at 15 - 25℃; for 1h; Industry scale; Stage #2: 7-Methoxy-1-tetralone In tetrahydrofuran; dimethyl sulfoxide at 15 - 25℃; for 2.5h; Product distribution / selectivity;	95%
Stage #1: 7-Methoxy-1-tetralone With sodium hydride In 1,2-dimethoxyethane at 15℃; for 0.5h; Stage #2: diethyl 1-cyanomethylphosphonate In monoethylene glycol diethyl ether at 10 - 15℃;	89%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 7-Methoxy-1-tetralone (6836-19-7) → trifluoromethanesulfonic acid 7-methoxy-3,4-dihydronaphthalen-1-yl ester (724707-85-1)

Conditions	Yield
Stage #1: 7-Methoxy-1-tetralone With lithium hexamethyldisilazane In tetrahydrofuran at -79℃; for 0.75h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 0℃; for 3h;	100%
With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 1h;	96%
With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 1.5h;	96%

7-Methoxy-1-tetralone (6836-19-7) → 7-methoxy-1,2,3,4-tetrahydro-1-naphthol (32820-10-3)

Conditions	Yield
With Tetrahydrofurfuryl alcohol; sodium tetrahydroborate; ethanol; (S,S)-(β-oxoaldiminato)cobalt(II) In chloroform at -20℃; for 12h;	99%
With sodium tetrahydroborate In ethanol at 20℃; Inert atmosphere;	99%
With methanol; sodium tetrahydroborate at 20℃;	98%

7-Methoxy-1-tetralone (6836-19-7) → 2-chloro-7-methoxy-3,4-dihydronaphthalen-1(2H)-one (85299-01-0)

Conditions	Yield
With 2,2,3,4,5,6-hexachloro-cyclohexa-2,4-dien-1-one In ethanol for 4h; Reflux;	99%
With 2,2,3,4,5,6-hexachloro-cyclohexa-2,4-dien-1-one In ethanol for 4h; Heating;	76%
Stage #1: 7-Methoxy-1-tetralone 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; thiourea In methanol at 35℃; for 2h; Inert atmosphere;

7-Methoxy-1-tetralone (6836-19-7) → 8-bromo-7-methoxy-1,2,3,4-tetrahydronaphthalen-1-one (61362-78-5)

Conditions	Yield
With iron(III) chloride; N-Bromosuccinimide In acetonitrile at 20℃; for 4h;	99%
With iron(III) chloride; N-Bromosuccinimide In acetonitrile at 20℃; for 10h;	98%
With N-Bromosuccinimide In acetonitrile at 20℃;	96%

7-Methoxy-1-tetralone (6836-19-7) → (-)-(R)-7-Methoxy-1-tetralol

Conditions	Yield
With C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; enantioselective reaction;	99%
With potassium tert-butylate; hydrogen; trans-RuCl2[(S)-XylBINAP][(R)-IPHAN] In isopropyl alcohol; tert-butyl alcohol at 25℃; under 6840 Torr; for 8h;	95%
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;	95%

7-Methoxy-1-tetralone (6836-19-7) → 1-methylene-7-methoxy-1,2,3,4-tetrahydronaphthalene (107727-34-4)

Conditions	Yield
With (bromomethyl)triphenyl-λ5-phosphane; potassium tert-butylate In tetrahydrofuran at 20 - 50℃; for 1h; Wittig Olefination; Inert atmosphere;	99%

7-Methoxy-1-tetralone (6836-19-7) + 2-(3,4,5-trimethoxybenzylidene)malononitrile (5688-82-4) → 2-amino-5,6-dihydro-9-methoxy-4-(3,4,5-trimethoxyphenyl)benzo[h]quinoline-3-carbonitrile

Conditions	Yield
With ammonium acetate; acetic acid In ethanol for 12h; Reflux;	99%

7-Methoxy-1-tetralone (6836-19-7) + acetonitrile (75-05-8) → 2-(1-hydroxyl-7-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetonitrile (59081-65-1)

Conditions	Yield
Stage #1: acetonitrile With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.5h; Stage #2: 7-Methoxy-1-tetralone In tetrahydrofuran; hexane at -70℃; for 1h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water Product distribution / selectivity;	98.4%
Stage #1: acetonitrile With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.5h; Cooling with ethanol-dry ice; Stage #2: 7-Methoxy-1-tetralone In tetrahydrofuran; hexane at -70℃; for 1h; Concentration; Cooling with ether-dry ice;	98.4%
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;	95%
Stage #1: 7-Methoxy-1-tetralone; acetonitrile With sodium hexamethyldisilazane In tetrahydrofuran at -80 - -70℃; for 0.75h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran

7-Methoxy-1-tetralone (6836-19-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 1-chloro-7-methoxy-3,4-dihydronaphthalene-2-carboxaldehyde (77664-95-0)

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.5h; Cooling with ice; Stage #2: 7-Methoxy-1-tetralone at 20 - 70℃; for 2h;	98.1%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at -10℃; Vilsmeier-Haack reaction; Reflux; Stage #2: 7-Methoxy-1-tetralone In N,N-dimethyl-formamide for 2h; Vilsmeier-Haack reaction; Reflux; Stage #3: With water; sodium acetate In N,N-dimethyl-formamide Vilsmeier-Haack reaction;	93%
With trichlorophosphate at 0 - 90℃; Vilsmeier-Haack Formylation;	91%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 20℃; Stage #2: 7-Methoxy-1-tetralone at 0 - 20℃; for 6h;	90%
With trichlorophosphate 1.) CH2Cl2, 27 deg C, 2 h, 2.) CH2Cl2, 27 deg C, 8 h; Yield given. Multistep reaction;

7-Methoxy-1-tetralone (6836-19-7) → 7-hydroxy-1-tetralone (22009-38-7)

Conditions	Yield
With hydrogen bromide; acetic acid In water at 120℃;	98%
Stage #1: 7-Methoxy-1-tetralone With aluminum (III) chloride In toluene at 20 - 65℃; for 2.6h; Stage #2: In toluene at 0 - 65℃; for 1.5h; Temperature;	96.4%
With aluminium trichloride In toluene Heating;	95%

trimethylsilyl cyanide (7677-24-9) + 7-Methoxy-1-tetralone (6836-19-7) → 7-methoxy-1-(trimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile (182621-29-0)

Conditions	Yield
With zinc(II) iodide In acetonitrile at 20℃; for 48h; Addition;	98%
With zinc(II) iodide In dichloromethane at 25℃; for 24h;
With zinc(II) iodide
With zinc(II) iodide In dichloromethane at 20℃;
With zinc(II) iodide In nitromethane at 0 - 20℃; for 96h; Inert atmosphere;

7-Methoxy-1-tetralone (6836-19-7) → (+)-(S)-7-Methoxy-1-tetralol (182965-69-1)

Conditions	Yield
With chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); formic acid; triethylamine In dichloromethane at 0 - 20℃; for 72h; Inert atmosphere; Schlenk technique; enantioselective reaction;	98%
With chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); formic acid; triethylamine In dichloromethane at 23℃; for 48h; Inert atmosphere; Cooling with ice; Schlenk technique;	98%
With formic acid; C29H38N3O2RuS; triethylamine at 60℃; for 4h; Inert atmosphere; enantioselective reaction;	96%

3-bromo-1-(4-ethylpiperazin-1-yl)isoquinoline (223552-79-2) + 7-Methoxy-1-tetralone (6836-19-7) → 3-(6-methoxy-1,2-dihydronaphthalen-4-yl)-1-(4-ethylpiperazin-1-yl)isoquinoline

Conditions	Yield
	98%

methyl magnesium iodide (917-64-6) + 7-Methoxy-1-tetralone (6836-19-7) → 1,2-dihydro-6-methoxy-4-methylnaphthalene (30021-91-1)

Conditions	Yield
Stage #1: methyl magnesium iodide; 7-Methoxy-1-tetralone In diethyl ether at 20℃; for 3h; Stage #2: With hydrogenchloride In water at 40℃; for 3h; pH=5;	97%
With diethyl ether Erhitzen des nach der Hydrolyse erhaltenen Reaktionsprodukts unter Normaldruck auf 100-110grad;
With diethyl ether Erhitzen des nach der Hydrolyse erhaltenen Reaktionsprodukts unter vermindertem Druck auf 120-160grad;

7-Methoxy-1-tetralone (6836-19-7) → 7-methoxy-1-d-1,2,3,4-tetrahydro-1-naphthol (199442-41-6)

Conditions	Yield
With sodium borodeuteride In methanol for 1.5h;	97%
With sodium borodeuteride

7-Methoxy-1-tetralone (6836-19-7) + allyl bromide (106-95-6) → 8a-allyl-7-methoxy-1,2,3,4,6,8a-hexahydro-naphthalen-1-one (310897-19-9) + 2,8a-diallyl-7-methoxy-3,4,6,8a-tetrahydro-2H-naphthalen-1-one

Conditions	Yield
Stage #1: 7-Methoxy-1-tetralone With ammonia; potassium In diethyl ether; tert-butyl alcohol at -78℃; for 0.25h; Reduction; Stage #2: With lithium bromide In diethyl ether; tert-butyl alcohol at -78℃; for 0.5h; deprotonation; Stage #3: allyl bromide In diethyl ether; tert-butyl alcohol at -78 - 20℃; Alkylation; Birch reductive alkylation;	A 97% B n/a

7-Methoxy-1-tetralone (6836-19-7) + phenyl trifluoromethanesulfonamide (456-64-4) → trifluoromethanesulfonic acid 7-methoxy-3,4-dihydronaphthalen-1-yl ester (724707-85-1)

Conditions	Yield
Stage #1: 7-Methoxy-1-tetralone With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Stage #2: phenyl trifluoromethanesulfonamide In tetrahydrofuran at 0℃; for 9h;	97%

7-Methoxy-1-tetralone (6836-19-7) + 1-((allyloxy)carbonyl)-1H-imidazole (83395-39-5) → allyl 7-methoxy-3,4-dihydronaphthalen-1-yl carbonate

Conditions	Yield
Stage #1: 7-Methoxy-1-tetralone With sodium hexamethyldisilazane In 1,2-dimethoxyethane at -78℃; for 1h; Inert atmosphere; Stage #2: 1-((allyloxy)carbonyl)-1H-imidazole With boron trifluoride diethyl etherate In 1,2-dimethoxyethane at -78℃; for 2.16667h; Inert atmosphere;	97%

7-Methoxy-1-tetralone (6836-19-7) + oxalic acid diethyl ester (95-92-1) → ethyl 2-(1-hydroxy-7-methoxy-3,4-dihydronaphthalen-2-yl)-2-oxoacetate (1417448-97-5)

Conditions	Yield
With lithium tert-butoxide In tetrahydrofuran at 0 - 20℃; for 4h; Claisen Condensation; Inert atmosphere;	97%

7-Methoxy-1-tetralone (6836-19-7) + cyanoacetic acid (372-09-8) → 2-(7-methoxy-3,4-dihydronaphthalen-1-yl)acetonitrile (861960-34-1)

Conditions	Yield
With oenanthic acid; benzylamine In toluene at 140℃; for 48h;	96.3%
With oenanthic acid; benzylamine In toluene Product distribution / selectivity; Heating / reflux;	90%
With oenanthic acid; benzylamine In toluene Product distribution / selectivity; Heating / reflux;	90%

7-methoxy-1,2,3,4-tetrahydro-1-naphthol (32820-10-3) + 7-Methoxy-1-tetralone (6836-19-7) → 7-methoxy-3,4-dihydronaphthalene (60573-58-2)

Conditions	Yield
	96%

7-Methoxy-1-tetralone (6836-19-7) + salicylaldehyde (90-02-8) → 2-methoxy-7H-benzo[c]xanthene (1289414-86-3)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In chlorobenzene at 180℃; for 0.5h; Microwave irradiation;	96%

7-Methoxy-1-tetralone (6836-19-7) + N-methoxylamine hydrochloride (593-56-6) → C12H15NO2

Conditions	Yield
With pyridine In ethanol for 1h; Inert atmosphere; Reflux;	96%

7-Methoxy-1-tetralone (6836-19-7) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → (E)-2-(3,4,5-trimethoxybenzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one

Conditions	Yield
With sodium methylate In methanol at 20℃;	96%
With sodium hydroxide In ethanol

7-Methoxy-1-tetralone (6836-19-7) → 6-methoxy-1,2,3,4-tetrahydronaphthalene (1730-48-9)

Conditions	Yield
With palladium dichloride In methanol at 40℃; for 24h; Inert atmosphere; Green chemistry;	95%
With potassium hydroxide; hydrazine hydrate In diethylene glycol for 0.333333h; Wolff-Kishner reduction; Irradiation;	87%
With hydrazine hydrate; sodium hydroxide In methanol at 200℃; under 37503.8 Torr; Wolff-Kishner Reduction; Microwave irradiation;	81%
With copper oxide-chromium oxide at 125 - 200℃; under 154457 Torr; Hydrogenolyse;
With hydrogenchloride; amalgamated zinc

7-Methoxy-1-tetralone (6836-19-7) + ethyl bromoacetate (105-36-2) → ethyl 1-hydroxy-7-methoxy-1,2,3,4-tetrahydro-1-naphthaleneacetate (99416-97-4)

Conditions	Yield
Stage #1: 7-Methoxy-1-tetralone; ethyl bromoacetate With zinc In tert-butyl methyl ether at 55 - 60℃; Reformatsky Reaction; Stage #2: With hydrogenchloride; water at 10 - 15℃;	95%
With toluene; zinc
With iodine; zinc In benzene for 2.5h; Reformatsky reaction; Heating;

Upstream product

• 32281-97-3 7-bromo-3,4-dihydro-2H-naphthalen-1-one 
• 38050-71-4 9-methoxy-9-BBN 
• 6836-18-6 4-(4-methoxyphenyl) butanoyl chloride 
• 4521-28-2 4-(4-Methoxyphenyl)butyric acid 
• 1202643-83-1 1-(3-methoxyphenyl)cyclobutan-1-ol 
• 2398-37-0 3-methoxyphenyl bromide 
• 75-91-2 tert.-butylhydroperoxide 
• 1730-48-9 6-methoxy-1,2,3,4-tetrahydronaphthalene 
• 24743-11-1 4-(m-methoxyphenyl)butanoic acid 
• 38102-67-9 4-(3-methoxy-phenyl)-4-oxo-butyric acid 
• 854278-66-3 C₁₃H₁₆O₃ 
• 1105703-75-0 C₁₃H₁₆O₃ 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 104-01-8 4-Methoxyphenylacetic acid 

Downstream Products

• 138206-93-6 dibenzyl 1-(1,2,3,4-tetrahydro-7-methoxy-1-oxo-2-naphthyl)-1,2-hydrazinedicarboxylate 
• 5302-79-4 7-methoxynaphthalen-1-amine 
• 87797-13-5 1,2,3,4-tetrahydro-7-methoxy-1-(4'-methoxyphenyl)naphthalene 
• 141247-30-5 2-(4-methoxybenzylidene)-7-methoxy-1-tetralone 
• 76290-92-1 7-Methoxy-6-(1-hydroxy-4-methoxybenzyl)-1-tetralol 
• 109381-27-3 2-Benzyl-7-methoxy-naphthalen-1-ol 
• 41526-55-0 2-phenylmethylene-7-methoxy-1-tetralone 
• 141247-31-6 2-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-7-methoxy-3,4-dihydro-2H-naphthalen-1-one 
• 76290-93-2 7-Methoxy-6--1-tetralol 
• 6273-71-8 7-methoxy-1-phenyl-3,4-dihydronaphthalene 
• 117356-91-9 N-benzyl-(1,2,3,4-tetrahydro-7-methoxy-1-oxonaphthalene-2-methyl)amine 
• 27331-38-0 7-methoxy-1-phenylnaphthalene 
• 20176-04-9 1-Acetoxy-7-methoxy-3.4-dihydro-naphthalin 
• 40077-02-9 7-Methoxy-2-(phenethylamino-methyl)-3,4-dihydro-2H-naphthalen-1-one 

Relevant articles and documents

Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe

A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.

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

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.]

Regioselective Electrochemical Cyclobutanol Ring Expansion to 1-Tetralones

A mild electrochemical method for the regioselective preparation of 1-tetralones under environmentally friendly conditions from readily available cyclobutanols was developed. A series of aromatic- and heteroaromatic-fused 1-tetralones was accessed through ring expansion of the functionalized cyclobutanols via electrochemical generation of alkoxy radicals and intramolecular cyclization.