2107-69-9

Basic information

• Product Name: 5,6-Dimethoxy-1-indanone
• Synonyms: 1H-Inden-1-one, 2,3-dihydro-5,6-dimethoxy-;5,6-Dimethoxy-2,3-dihydro-1H-indene-1-one;5,6-Dimethoxyindan-1-one 98%;5,6-Dimethoxy-1-inda;2,3-Dihydro-5,6-diMethoxy-;Donepezil IMpurity (Indanone IMpurity);2,3-Dihydro-5,6-dimethoxy-1H-inden-1-one, 2,3-Dihydro-5,6-dimethoxy-1-oxo-1H-indene;5,6- twoMethoxy -1-indone
• CAS NO: 2107-69-9
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21
• EINECS: 218-287-8
• Product Categories: Intermediates;Indane/Indanone and Derivatives;Indanone & Indene;API intermediates;Aromatics Compounds;Intermediates of Donepezil;Aromatics;C11 to C12;Carbonyl Compounds;Ketones
• Mol File: 2107-69-9.mol
• Article Data: 35

Chemical Properties

• Melting Point: 118120°C
• Boiling Point: 139 °C / 2mmHg
• Flash Point: 150.4 °C
• Appearance: white to light yellow crystal powder
• Density: 1.1503 (rough estimate)
• Vapor Pressure: 3.35E-06mmHg at 25°C
• Refractive Index: 1.4600 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Ethyl Acetate
• BRN: 1241095
• CAS DataBase Reference: 5,6-Dimethoxy-1-indanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dimethoxy-1-indanone(2107-69-9)
• EPA Substance Registry System: 5,6-Dimethoxy-1-indanone(2107-69-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 2107-69-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 2107-69-9 differently. You can refer to the following data:
1. 5,6-Dimethoxy-1-indanone can be an intermediate useful in the preparation of Donepezil.
2. 5,6-Dimethoxy-1-indanone was used in the synthesis of 2,3-dimethoxy-11H-indeno[1,2-b]quinoline-6,10-dicarboxylic acid.

General Description

Thiosemicarbazone derived from 5,6-dimethoxy-1-indanone inhibits bovine viral diarrhea virus infection.

Purification Methods

Crystallise the indanone from MeOH, then sublime it in a vacuum. [Beilstein 8 IV 1985.]

InChI:InChI=1/C9H10N2O2/c1-12-8-3-6-7(11-5-10-6)4-9(8)13-2/h3-5H,1-2H3,(H,10,11)

Synthetic route

3,4-methoxycinnamic acid (2107-70-2) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 80℃; for 1h; Friedel-Crafts Acylation; High pressure; Inert atmosphere; Green chemistry;	100%
With trifluorormethanesulfonic acid In dichloromethane at 0 - 80℃;	100%
With trifluorormethanesulfonic acid In dichloromethane at 0 - 80℃; for 1.5h; Sealed tube;	96%

2-ethenyl-4,5-dimethoxybenzaldehyde (52095-39-3) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine In toluene at 150℃; for 1h; Inert atmosphere;	98%
With acetic acid; L-proline at 120℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Green chemistry;	90%

6-hydroxy-5-methoxyindan-1-one (90843-62-2) + methyl iodide (74-88-4) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
Stage #1: 6-hydroxy-5-methoxyindan-1-one With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 1h;	90.1%

carbon monoxide (201230-82-2) + 1-iodo-4,5-dimethoxy-2-vinylbenzene → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With pyridine; palladium diacetate; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; under 760 Torr; for 24h;	82%

3-(3,4-dimethoxy-phenyl)-propionyl chloride (51842-87-6) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With rhenium(I) pentacarbonyl bromide In 1,2-dichloro-ethane for 2h; Heating;	80%
With aluminium trichloride In dichloromethane at 20℃; for 3h;	40.2 g
With aluminum (III) chloride In dichloromethane at 20℃; for 2h;

(5,6-dimethoxyindan-1-yl)methanol → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With silica gel; pyridinium chlorochromate In dichloromethane at 25℃; for 6h;	72%

dimethyl 2-((3-(3,4-dimethoxyphenyl)propanoyl)oxy)succinate (64803-82-3) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel-Crafts Acylation; Inert atmosphere; regioselective reaction;	70%

1-bromo-4,5-dimethoxy-2-vinylbenzene (5293-43-6) + molybdenum hexacarbonyl → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With pyridine; tetrabutyl-ammonium chloride; tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate In N,N-dimethyl-formamide at 130℃; for 0.333333h; microwave irradiation;	67%

3,4-methoxycinnamic acid (2107-70-2) → 5,6-dimethoxy-1-indanone (2107-69-9) + 6,7-dimethoxy-2,3-dihydro-1H-inden-1-one (57441-74-4)

Conditions	Yield
With terbium(III) trifluoromethanesulfonate In chlorobenzene at 250℃; for 1h; Friedel-Crafts reaction;	A 65% B 5%

5-(3,4-dimethoxybenzyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione (154317-78-9) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In nitromethane at 100℃; for 0.75h; Friedel-Crafts acylation;	59%

1,2-dimethoxybenzene (91-16-7) + N,N-Dimethylacrylamide (2680-03-7) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With trifluoromethanesulfonic acid anhydride In 1,2-dichloro-ethane for 6h; Heating;	42%
With trifluoromethylsulfonic anhydride; potassium carbonate 1.) dichloroethane, reflux, 6 h, 2.) dichloroethane, ether, 1 h; Yield given. Multistep reaction;

1-(3,4-dimethoxyphenyl)prop-2-en-1-one (33731-40-7) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane for 5h; Heating;	3.4%

6,7-dimethoxy-1-oxo-1H-isothiochromene-3-carboxylic acid (56661-87-1) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With nickel

5,6-dimethoxy-3-oxo-indan-1-carboxylic acid (62956-63-2) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With quinoline; copper at 230℃;

5,6-dimethoxy-1H-indene (40243-67-2) → 5,6-dimethoxy-1-indanone (2107-69-9) + 5,6-dimethoxy-1H-inden-2(3H)-one (30117-82-9)

Conditions	Yield
With diborane In tetrahydrofuran a) 0 deg C, 15 min, b) 20 deg C, 45 min;
With diborane In tetrahydrofuran a) 0 deg C, 15 min, b) 20 deg C, 45 min; Title compound not separated from byproducts;

ethanol (64-17-5) + 6,7-dimethoxy-1-oxo-1H-isothiochromene-3-carboxylic acid (56661-87-1) + Raney nickel → 5,6-dimethoxy-1-indanone (2107-69-9)

dimethyl sulfate (77-78-1) + 6-oxy-5-methoxy-hydrindone-(1) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
With alkaline solution

3,4-methoxycinnamic acid (2107-70-2) + benzene (71-43-2) + P2O5 → 5,6-dimethoxy-1-indanone (2107-69-9)

phosphorus pentachloride (10026-13-8, 874483-75-7) + 3,4-methoxycinnamic acid (2107-70-2) + petroleum ether → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
Behandlung des entstandenen Chlorids mit AlCl3;

sulfuric acid (7664-93-9) + 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-indene-2-carbonitrile (106648-24-2) → 5,6-dimethoxy-1-indanone (2107-69-9)

1-(3-Hydroxy-phenoxy)-5,6-dimethoxy-indan-1-ol + diluted NaOH-solution → 5,6-dimethoxy-1-indanone (2107-69-9) + recorcinol (108-46-3)

3-(3,4-dimethoxyphenyl)propanoic acid sodium salt → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl chloride; DMF / CH2Cl2 2: 40.2 g / AlCl3 / CH2Cl2 / 3 h / 20 °C View Scheme

3,4-dimethoxy-benzaldehyde (120-14-9) + polymer-PPh2(1+)-CH2-Ph*Br(1-) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: piperidinium acetate / ethanol / 0.5 h 1.2: 77 percent / NaBH3CN / ethanol / 0 - 20 °C 2.1: 59 percent / Sc(OTf)3 / nitromethane / 0.75 h / 100 °C View Scheme

2-iodo-4,5-dimethoxybenzaldehyde (61203-53-0) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C 1.2: 90 percent / tetrahydrofuran 2.1: 82 percent / Pd(OAc)2; pyridine; n-Bu4NCl / dimethylformamide / 24 h / 100 °C / 760 Torr View Scheme

5,6-dimethoxy-2,3-dihydro-1H-inden-1-ol (33884-52-5) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethyl sulfoxide / 6 h / 180 °C 2: diborane / tetrahydrofuran / a) 0 deg C, 15 min, b) 20 deg C, 45 min View Scheme

3,4-dimethoxycinnamic acid (2316-26-9) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium amalgam; alkali 2: benzene; P2O5 View Scheme
Multi-step reaction with 2 steps 1: H2 / Raney-Ni / ethanol / 100 °C / 66195.7 Torr 2: H3PO4, P2O5 View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 14 h / 60 °C / 114008 Torr 2: phosphorus pentoxide; phosphoric acid / 6 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 40 °C 2: trifluorormethanesulfonic acid / dichloromethane / 1 h / 80 °C View Scheme

3,4-dimethoxy-trans-cinnamic acid (14737-89-4) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: platinum; acetic acid / Hydrogenation 2: HF View Scheme

3,4-dimethoxy-cinnamic acid ethyl ester (20583-78-2) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide; methanol 2: sodium amalgam; alkali 3: benzene; P2O5 View Scheme

3,4-dimethoxy-benzaldehyde (120-14-9) → 5,6-dimethoxy-1-indanone (2107-69-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) Py, (ii) aq. HCl 2: H2 / Raney-Ni / ethanol / 100 °C / 66195.7 Torr 3: H3PO4, P2O5 View Scheme
Multi-step reaction with 2 steps 1: triethylammonium formate / N,N-dimethyl-formamide / 6 h / 20 °C 2: polyphosphoric acid / 2 h / 20 - 100 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine / 16 h / 80 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 14 h / 60 °C / 114008 Torr 3: phosphorus pentoxide; phosphoric acid / 6 h / 120 °C View Scheme

5,6-dimethoxy-1-indanone (2107-69-9) + carbonic acid dimethyl ester (616-38-6) → 5,6-dimethoxy-2-methoxycarbonylindan-1-one (119035-03-9)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil Reflux; Inert atmosphere;	100%
With sodium hydride In paraffin oil at 90℃;	92%
With sodium hydride In paraffin oil at 90℃; Inert atmosphere;	92%

5,6-dimethoxy-1-indanone (2107-69-9) + 1-benzyl-4-formylpiperidine (22065-85-6) → 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine (120014-07-5)

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water; toluene at 20℃; Product distribution / selectivity; Inert atmosphere; Reflux;	100%
With sodium methylate In methanol; ethanol at 79℃; for 1.58333h; Product distribution / selectivity; Heating / reflux;	93.4%
With sodium methylate In methanol at 66℃; for 1h; Product distribution / selectivity; Heating / reflux;	93.9%

5,6-dimethoxy-1-indanone (2107-69-9) → 5,6-dihydroxy-indan-1-one (124702-80-3)

Conditions	Yield
With boron tribromide In chloroform at -78℃; for 4h;	100%
With boron tribromide In dichloromethane	98%
With boron tribromide In dichloromethane at -78 - 20℃; for 1h;	98%

5,6-dimethoxy-1-indanone (2107-69-9) → 5,6-dimethoxy-1H-inden-1,2(3H)-dione 2-oxime

Conditions	Yield
	100%

5,6-dimethoxy-1-indanone (2107-69-9) + p-nitrophenyl isothiocyanate (2131-61-5) → 5,6-dimethoxyindan-1-one N-(4-nitrophenyl)thiosemicarbazone

Conditions	Yield
With hydrazine hydrate; acetic acid In isopropyl alcohol at 90℃; under 1875.19 Torr; for 1.08333h; Microwave irradiation;	100%

5,6-dimethoxy-1-indanone (2107-69-9) + piperonal (120-57-0) → 2-[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-5,6-dimethoxy-indan-1-one

Conditions	Yield
With sodium hydroxide In ethanol for 0.0125h; Irradiation;	99%

piperidine (110-89-4) + 5,6-dimethoxy-1-indanone (2107-69-9) → 1-(5,6-dimethoxy-1H-inden-3-yl)piperidine

Conditions	Yield
With titanium tetrachloride In toluene at -10 - 20℃; Inert atmosphere;	99%

5,6-dimethoxy-1-indanone (2107-69-9) → 2-bromo-5,6-dimethoxy-1-indanone (2747-08-2)

Conditions	Yield
With bromine In ethyl acetate at 10 - 20℃; for 0.5h;	98%
With bromine In methanol at 20℃; for 0.5h;	84%
With copper(ll) bromide In ethyl acetate Reflux;	81%

5,6-dimethoxy-1-indanone (2107-69-9) + 5-chloroindole 2,3-dione (17630-76-1) → 5-Chloro-3-[5,6-dimethoxy-1-oxo-indan-(2E)-ylidene]-1,3-dihydro-indol-2-one

Conditions	Yield
With hydrogenchloride In acetic acid at 100℃; for 1.25h;	98%

5,6-dimethoxy-1-indanone (2107-69-9) + 2-chloro-6-methoxyquinolin-3-carboxaldehyde (73568-29-3) → 2-[1-(2-Chloro-6-methoxy-quinolin-3-yl)-meth-(E)-ylidene]-5,6-dimethoxy-indan-1-one

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 12h;	98%

pyridine-4-carbaldehyde (872-85-5) + 5,6-dimethoxy-1-indanone (2107-69-9) → (E)-5, 6-dimethoxy-2-(pyridin-4-ylmethylene)-2, 3-dihydro-1H-inden-1-one (877606-65-0)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 6h; Reflux;	98%
With toluene-4-sulfonic acid In toluene for 6h; Heating;	95.6%
With toluene-4-sulfonic acid In toluene for 6h; Reflux;	90%

pyridine-4-carbaldehyde (872-85-5) + 5,6-dimethoxy-1-indanone (2107-69-9) → 5,6-dimethoxy-2-[(pyridin-4-yl)methylene]-1-indanone (4803-74-1)

Conditions	Yield
With potassium hydroxide In water at 25 - 30℃; for 3h; Product distribution / selectivity;	98%
Stage #1: pyridine-4-carbaldehyde; 5,6-dimethoxy-1-indanone With toluene-4-sulfonic acid In toluene for 6h; Heating / reflux; Stage #2: With sodium carbonate In water for 0.5 - 1h;	95.8%
With potassium iodide; calcium chloride In acetone at 40 - 50℃; for 4h; Reagent/catalyst; Time;	92.2%

5,6-dimethoxy-1-indanone (2107-69-9) + Diethyl carbonate (105-58-8) → 5,6-(dimethoxy)-2-(ethoxycarbonyl)-indan-1-one (53295-44-6)

Conditions	Yield
Stage #1: Diethyl carbonate With sodium hydride In tetrahydrofuran; oil for 1.5h; Heating / reflux; Stage #2: 5,6-dimethoxy-1-indanone In tetrahydrofuran; oil for 3h; Heating / reflux;	98%
Stage #1: Diethyl carbonate With sodium hydride In tetrahydrofuran for 1.5h; Heating / reflux; Stage #2: 5,6-dimethoxy-1-indanone In tetrahydrofuran for 3h; Heating / reflux;	98%
With sodium hydride In toluene; mineral oil for 6h; Reflux;	85%

5,6-dimethoxy-1-indanone (2107-69-9) + benzyl alcohol (100-51-6) → 2-benzyl-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (74402-02-1)

Conditions	Yield
With potassium phosphate tribasic trihydrate; C39H32Cl2N5PRu In tert-Amyl alcohol at 120℃; for 4h; Inert atmosphere; Schlenk technique;	98%
With trifuran-2-yl-phosphane; C48H34F6N4O4Pd2; lithium hydroxide In neat (no solvent) at 100℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;	92%

5,6-dimethoxy-1-indanone (2107-69-9) + 4-Methylbenzyl alcohol (589-18-4) → 5,6-dimethoxy-2-(4-methylbenzyl)-2,3-dihydro-1H-inden-1-one

Conditions	Yield
With potassium phosphate tribasic trihydrate; C39H32Cl2N5PRu In tert-Amyl alcohol at 120℃; for 4h; Inert atmosphere; Schlenk technique;	98%

5,6-dimethoxy-1-indanone (2107-69-9) + methyllithium (917-54-4) → 5,6-dimethoxy-3-methyl-1H-indene (127600-31-1)

Conditions	Yield
In tetrahydrofuran; diethyl ether for 16h; Ambient temperature; -55 deg C to room temperature;	97%

5,6-dimethoxy-1-indanone (2107-69-9) → 3-bromo-5,6-dimethoxy-1-indanone (537690-41-8)

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2.5h; Heating;	97%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4h; Reagent/catalyst; Solvent; Reflux;	80.4%

5,6-dimethoxy-1-indanone (2107-69-9) + 2-butenyloxyamine hydrochloride (113211-42-0) → 5,6-dimethoxyindan-1-one oxime O-crotyl ether

Conditions	Yield
With sodium acetate In ethanol for 2h; Heating;	95%

5,6-dimethoxy-1-indanone (2107-69-9) → 5,6-dimethoxy-indan-1,2-dione-2-oxime (2107-85-9)

Conditions	Yield
With hydrogenchloride; n-Butyl nitrite In methanol at 40℃; for 0.5h;	95%
With hydrogenchloride; n-Butyl nitrite In methanol; water at 40℃; for 2.5h;	93%
With hydrogenchloride; n-Butyl nitrite In methanol at 40℃; for 0.5h;	92%

5,6-dimethoxy-1-indanone (2107-69-9) → 2,4-dibromo-5,6-dimethoxyindan-1-one

Conditions	Yield
With bromine In acetic acid at 20℃; for 2h;	95%

5,6-dimethoxy-1-indanone (2107-69-9) + 4-benzaldehyde → 2-(4-(4-(2-hydroxyethyl)piperazin-1-yl)benzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 48h; Claisen-Schmidt Condensation;	95%

5,6-dimethoxy-1-indanone (2107-69-9) + 1,1-dimethylhydrazine (57-14-7) → 2-(5,6-dimethoxy-2,3-dihydro-1H-inden-1-ylidene)-1,1-dimethylhydrazine

Conditions	Yield
With trifluoroacetic acid In benzene Reflux; Dean-Stark; Inert atmosphere;	95%

5,6-dimethoxy-1-indanone (2107-69-9) → 5,6-dimethoxyindane (59078-28-3)

Conditions	Yield
With hydrogenchloride; mercury; zinc In water; toluene for 6h; Heating;	94%
With amalgamated zinc	71%
With hydrogenchloride; mercury; zinc

5,6-dimethoxy-1-indanone (2107-69-9) + 5-nitroisatin (611-09-6) → 3-[5,6-Dimethoxy-1-oxo-indan-(2E)-ylidene]-5-nitro-1,3-dihydro-indol-2-one

Conditions	Yield
With hydrogenchloride In acetic acid at 100℃; for 1.25h;	94%

5,6-dimethoxy-1-indanone (2107-69-9) + indole-2,3-dione (91-56-5) → 2,3-dimethoxy-11H-indeno<1,2-b>quinoline-10-carboxylic acid

Conditions	Yield
With hydrogenchloride In acetic acid at 105℃; for 16h;	94%

5,6-dimethoxy-1-indanone (2107-69-9) + 2-chloro-5,6,7-trimethoxyquinoline-3-carboxaldehyde (68236-25-9) → 2-[1-(2-Chloro-5,6,7-trimethoxy-quinolin-3-yl)-meth-(E)-ylidene]-5,6-dimethoxy-indan-1-one

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 12h;	94%

5,6-dimethoxy-1-indanone (2107-69-9) + 4-Phenylbenzaldehyde (3218-36-8) → 2-([1,1′-biphenyl]-4-ylmethylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Conditions	Yield
With potassium hydroxide In ethanol; water at 50℃; for 72h;	93.8%

5,6-dimethoxy-1-indanone (2107-69-9) → 5,6-dimethoxy-1-aminoindane (91247-06-2)

Conditions	Yield
With ammonia; hydrogen In ethanol at 100℃; under 3750.38 - 33753.4 Torr; Pressure; Autoclave;	93.3%
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride, NaOH, H2O / ethanol / 0.33 h / Heating 2: Raney nickel, NaOH, H2O / ethanol / 1 h View Scheme

Upstream product

• 56661-87-1 6,7-dimethoxy-1-oxo-1H-isothiochromene-3-carboxylic acid 
• 40243-67-2 5,6-dimethoxy-1H-indene 
• 5293-43-6 1-bromo-4,5-dimethoxy-2-vinylbenzene 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 52095-39-3 2-ethenyl-4,5-dimethoxybenzaldehyde 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 4693-38-3 3-chloro-1-(3,4-dimethoxyphenyl)propan-1-one 
• 90843-62-2 6-hydroxy-5-methoxyindan-1-one 
• 74-88-4 methyl iodide 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 64803-82-3 dimethyl 2-((3-(3,4-dimethoxyphenyl)propanoyl)oxy)succinate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 130489-93-9 5,6-dimethoxyindan-1-carbonitrile 
• 909806-49-1 2,2-dibromo-5,6-dimethoxyindan-1-one 
• 120014-06-4 donepezil 
• 18028-27-8 5,6-dimethoxy-1-indanone phenylhydrazone 
• 36517-91-6 2,3-dihydro-5,6-dimethoxy-1H-indene-1,3-dione 
• 582292-91-9 2-amino-4-(2,4-dichloro-phenyl)-7,8-dimethoxy-5H-indeno[1,2-b]pyridine-3-carbonitrile 
• 127399-78-4 5-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one 
• 90843-62-2 6-hydroxy-5-methoxyindan-1-one 

Relevant articles and documents

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A metal-free method for the facile synthesis of indanonesviathe intramolecular hydroacylation of 2-vinylbenzaldehyde

A facile method for the synthesis of indanones was developed under metal- and additive-free conditions, whereinl-proline served as an efficient and environmentally benign catalyst. Compared with previously synthesized indanones, synthesis by the transition-metal-catalyzed intramolecular hydroacylation of 2-vinylbenzaldehyde provided a more green synthetic pathway to indanone scaffolds with good to excellent yields. More importantly, it could be used to synthsize the anti-AD drug donepezil.

Trifluoroacetic Anhydride Mediated One-Pot Synthesis of 1-Aryl Isochroman-3-ones via the Carboxy-Pictet-Spengler Reaction

In this paper, a novel and open-vessel route for the facile-operational synthesis of 1-aryl isochroman-3-ones is described via (CF3CO)2O (trifluoroacetic anhydride, TFAA)-mediated intermolecular (4 + 2) annulation of oxygenated arylacetic acids with arylaldehydes or ketones under mild reaction conditions. A plausible mechanism is proposed and discussed herein. Various reaction conditions are investigated for efficient transformation under an environmentally friendly one-pot carboxy-Pictet-Spengler reaction.