86-55-5

Basic information

• Product Name: 1-Naphthoic acid
• Synonyms: LABOTEST-BB LT00855493;a-naphthoic acid;ALPHA-NAPHTHOIC ACID;1-NAPHTHALENECARBOXYLIC ACID;1-NAPHTHOIC ACID;1-NAPTHOIC ACID;RARECHEM AL BO 0197;α-Naphthoic acid
• CAS NO: 86-55-5
• Molecular Formula: C₁₁H₈O₂
• Molecular Weight: 172.18
• EINECS: 201-681-9
• Product Categories: Aromatic Compounds;Naphthalene derivatives;Organic acids;Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;intermediates;Naphthalene series;Fluorescent;Naphthalene
• Mol File: 86-55-5.mol
• Article Data: 212

Chemical Properties

• Melting Point: 157-160 °C(lit.)
• Boiling Point: 300 °C(lit.)
• Flash Point: 195°C
• Appearance: Slightly yellow to brown/Powder
• Density: 1.398
• Vapor Pressure: 0.000513mmHg at 25°C
• Refractive Index: 1.4600 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Solubility Slightly soluble in hot water; freely soluble in hot
• PKA: 3.7(at 25℃)
• Water Solubility: Freely soluble in hot alcohol and ether. Slightly soluble in hot water.
• Stability: Stable. Incompatible with strong bases, strong oxidizing agents.
• Merck: 14,6381
• BRN: 1908896
• CAS DataBase Reference: 1-Naphthoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthoic acid(86-55-5)
• EPA Substance Registry System: 1-Naphthoic acid(86-55-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-37
• WGK Germany: 2
• RTECS: QL0960000
• TSCA: Yes
• Hazardous Substances Data: 86-55-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to beige powder

Uses

1-Naphthoic acid is used as an intermediate for the synthesis of pharmaceuticals, photochemicals, plant growth hormones, dyes and other organic compounds.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 425, 1943Tetrahedron Letters, 22, p. 1013, 1981 DOI: 10.1016/S0040-4039(01)82853-7

Purification Methods

Crystallise the acid from toluene (3mL/g) (charcoal), pet ether (b 80-100o), or aqueous 50% EtOH. The amide has m 202o (from EtOH). [Beilstein 9 IV 2402.]

InChI:InChI=1/C11H8O2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H,12,13)/p-1

Synthetic route

1,8-Naphthalic anhydride (81-84-5) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
Stage #1: 1,8-Naphthalic anhydride With sodium hydroxide In water at 100℃; for 0.0166667h; microwave irradiation; Stage #2: With mercury(II) diacetate In water at 200℃; for 0.25h; Pesci reaction; microwave irradiation; Stage #3: With hydrogenchloride In water at 120℃; for 0.25h; microwave irradiation;	100%

carbon monoxide (201230-82-2) + 1-Bromonaphthalene (90-11-9) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With sodium hydroxide; cobalt(II) acetate In ethanol at 65℃; under 1520 Torr; for 4h; Irradiation;	99.3%
With sodium hydroxide; tetrabutylammomium bromide; dicobalt octacarbonyl In water; benzene at 65℃; under 760 Torr; for 5h; Irradiation;	96%
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 4.5h; Irradiation;	95%
With tributyl-amine; water; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride at 110 - 130℃; under 3 Torr; for 24h;	48%
With water; sodium acetate; triethylamine; Pd-bis(1-methylbenzothiazole-2-carbene) In N,N-dimethyl acetamide at 130℃; for 7h;	55 % Chromat.

1-naphthaldehyde (66-77-3) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube;	99%
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;	99%
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃;	98%

(1-nosyl-5-nitroindol-3-yl)methyl 1-naphthoate → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
Stage #1: (1-nosyl-5-nitroindol-3-yl)methyl 1-naphthoate With 2-(N,N-dimethylamino)ethylthiol hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.25h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water; acetonitrile Inert atmosphere;	99%

benzyl 1-naphthoate (53422-19-8) + toluene (108-88-3) → 1-naphthalenecarboxylic acid (86-55-5) + 1-methyl-3-(phenylmethyl)-benzene (620-47-3) + 1-methyl-4-(phenylmethyl)benzene (620-83-7) + 2-benzyltoluene (713-36-0)

Conditions	Yield
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction;	A 99% B n/a C n/a D n/a

1-Bromonaphthalene (90-11-9) + sodium methyl carbonate (6482-39-9) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
Stage #1: 1-Bromonaphthalene With iodine; magnesium In tetrahydrofuran at 60℃; for 17.25h; Inert atmosphere; Stage #2: sodium methyl carbonate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	99%

carbon dioxide (124-38-9) + 1-Fluoronaphthalene (321-38-0) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
Stage #1: 1-Fluoronaphthalene With C78H70Al2Cl4N6P4Rh2; magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 22h; Inert atmosphere; Glovebox; Stage #2: carbon dioxide In tetrahydrofuran at 20℃; under 760.051 Torr; for 0.5h; Reagent/catalyst; Temperature;	99%

1-naphthalene methanol (4780-79-4) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With N-Bromosuccinimide; oxygen In acetonitrile at 20℃; for 10h; Irradiation;	97%
With periodic acid; pyridinium chlorochromate In acetonitrile	96%
With tert.-butylhydroperoxide; manganese(II) acetate; trifluoroacetic acid In acetonitrile at 80℃; under 15001.5 Torr; for 13h; Mechanism; chemoselective reaction;	95%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + 1-naphthyl triflate (99747-74-7) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;	97%

formic acid (64-18-6) + 1-Iodonaphthalene (90-14-2) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere; Sealed tube;	97%
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;	75%

2-(azulen-6-yl)ethyl 1-naphthoate → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 3h;	97%

carbon dioxide (124-38-9) + 1-Bromonaphthalene (90-11-9) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With potassium; potassium iodide; magnesium chloride In tetrahydrofuran 1.) reflux, 1 h, 2.) -3 deg C, 4.5 h;	96%
With C26H30B10Cl2P2Pd In toluene at 50℃; under 760.051 Torr; for 10h;	91%
With diethylzinc; palladium diacetate; tert-butyl XPhos In hexanes; N,N-dimethyl acetamide at 40℃; under 7600.51 Torr; Automated synthesizer;	69%
With manganese; 2.9-dimethyl-1,10-phenanthroline; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;	68%
With 6,6'-dimethyl-2,2'-bipyridine; lithium chloride; cobalt(II) iodide; zinc In N,N-dimethyl-formamide; acetonitrile at 40℃; under 760.051 Torr; for 14h; Sealed tube;	46%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + naphthalen-1-yl 2,3,4,5,6-pentafluorobenzenesulfonate → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;	96%

4-((tert-butyldimethylsilyl)oxy)benzyl 1-naphthoate → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h;	95%

carbon monoxide (201230-82-2) + 1-Chloronaphthalene (90-13-1) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With dicobalt octacarbonyl; potassium carbonate; methyloxirane In methanol at 60℃; under 760 Torr; for 2.5h;	92%
With potassium hydroxide; (bis(tricyclohexyl)phosphine)palladium(II) dichloride In water for 72h; Heating;	10300 % Turnov.
With dicobalt octacarbonyl; potassium carbonate; benzyl chloride at 60℃; under 760 Torr; for 0.5h; carbonylation of aryl bromides, relative reactivity, effect of cocatalysts;

naphth-1-yl acetic acid (86-87-3) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile at 25℃; for 10h; UV-irradiation;	92%
With iodine; dimethyl sulfoxide at 120℃; for 26h; Sealed tube; Green chemistry;	88%

1-(4-methoxyphenyl)-2-(naphthalen-1-yl)ethan-1-one (76580-08-0) → 1-naphthalenecarboxylic acid (86-55-5) + 4-methoxybenzoic acid (100-09-4)

Conditions	Yield
With oxygen; potassium hydroxide at 20℃; Schlenk technique; chemoselective reaction;	A 92% B 92%

carbon monoxide (201230-82-2) + 1-naphthyl triflate (99747-74-7) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With potassium acetate; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In dimethyl sulfoxide at 60℃; for 3h;	90%

carbon monoxide (201230-82-2) + 1-Iodonaphthalene (90-14-2) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; bis-triphenylphosphine-palladium(II) chloride; water; sodium carbonate In water at 100℃; under 7600.51 Torr; for 24h; Catalytic behavior; Autoclave;	90%
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 5h;	87%
With water; potassium carbonate In acetonitrile at 100℃; under 3750.38 Torr; for 0.0161111h;	87%
With water; palladium diacetate; triethylamine; triphenylphosphine In 1,4-dioxane at 110℃; under 11251.1 Torr; for 2h; Flow reactor;	43%

carbon monoxide (201230-82-2) + 1-Bromonaphthalene (90-11-9) → 1-naphthalenecarboxylic acid (86-55-5) + 1-naphthylglycolic acid (6341-54-4) + 1-naphthylglyoxylic acid (26153-26-4)

Conditions	Yield
With methyl iodide; sodium sulfide In water; isopropyl alcohol at 20℃; for 20h;	A 6% B 3% C 89%
With methyl iodide; sodium sulfide In water; isopropyl alcohol at 60℃; for 20h;	A 60% B 17% C 20%
With sodium sulfide; CoCl2 In 1,4-dioxane; water at 20℃; for 20h; Product distribution; other reag.; other solvent;	A 4 % Chromat. B 9 % Chromat. C 86 % Chromat.

1-Iodonaphthalene (90-14-2) + lithium formate (556-63-8) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With acetic anhydride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal In N,N-dimethyl-formamide at 100℃; for 10h;	89%
Stage #1: lithium formate With acetic anhydride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Stage #2: 1-Iodonaphthalene With tris(dibenzylideneacetone)dipalladium (0); lithium chloride In N,N-dimethyl-formamide at 80℃; for 6h;	82%

(±)-1,2-di(naphthalen-1-yl)ethane-1,2-diol (84812-40-8) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With sodium hypochlorite In acetonitrile at 20℃; for 18h;	89%

carbon dioxide (124-38-9) + 1-lithiothionaphthalene*TMEDA complex → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
In Petroleum ether -100 deg C to 0 deg C;	88%

1H-cyclobutanaphthalen-1-one (85924-97-6) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With potassium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide for 3.5h; further reagents;	88%

methyl 1-naphthoate (2459-24-7) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With potassium hydroxide In methanol at 35℃; for 1h;	87%
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 83.3℃; Rate constant; substituents polar effects;

carbon dioxide (124-38-9) + 1-Iodonaphthalene (90-14-2) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene; cesium fluoride In N,N-dimethyl-formamide at 0 - 20℃; under 760.051 Torr; for 2h;	87%
With copper(l) iodide; diethylzinc; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 70℃; under 760.051 Torr;	68%

C26H18N2O6S + thiophenol (108-98-5) → 3-<(phenylthio)methyl>-1H-indole (56366-43-9) + 1-naphthalenecarboxylic acid (86-55-5) + 2-nitrophenyl phenyl sulfide (4171-83-9)

Conditions	Yield
With caesium carbonate In acetonitrile Inert atmosphere;	A 84% B 82% C 86%

bis(naphthalen-1-yl)methanone (605-78-7) → naphthalene (91-20-3) + 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With potassium hydroxide In 1,2-dimethoxyethane	A 70% B 85%

1,2-bis(naphthalen-1-yl)ethane-1,2-dione (3457-41-8) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With sodium hypochlorite In acetonitrile at 20℃; for 1.5h;	85%
With 2-(3-thiazolium)-1-phenylethanone bromide; triethylamine In dimethyl sulfoxide; acetonitrile at 37℃; Acidic conditions;

1-(1-naphthyl)ethanol (57605-95-5) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With sodium nitrate; water; oxygen In dimethyl sulfoxide at 130℃; for 36h;	85%

1-naphthalenecarboxylic acid (86-55-5) → naphthalene-1-carbonic acid chloride (879-18-5)

Conditions	Yield
With thionyl chloride In toluene for 2h; Reflux;	100%
With thionyl chloride for 2h; Heating / reflux;	98%
With thionyl chloride for 2h; Heating;	98%

1-naphthalenecarboxylic acid (86-55-5) + ethyl iodide (75-03-6) → ethyl 1-naphthoate (3007-97-4)

Conditions	Yield
With caesium carbonate In acetonitrile for 1.5h; Heating;	100%
With caesium carbonate In acetonitrile at 20℃; for 1.5h; Reflux; Inert atmosphere;	79%
With caesium carbonate In acetonitrile at 20℃; for 90h; Reflux; Inert atmosphere;	79%
With 18-crown-6 ether; potassium carbonate In tetrahydrofuran for 21h; Inert atmosphere; Reflux;

1-naphthalenecarboxylic acid (86-55-5) + [(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol (257299-95-9) → ((1R,3S)-5-iodo-6,8-dimethoxy-1-methyl-2-tosyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl 1-naphthoate (1248682-79-2)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere;	100%

1-naphthalenecarboxylic acid (86-55-5) → cis-cis-decahydro-1-naphthoic acid (6240-39-7, 7384-42-1, 15177-65-8, 20698-65-1)

Conditions	Yield
With platinum(IV) oxide; hydrogen In acetic acid under 3000.3 Torr;	100%

1-naphthalenecarboxylic acid (86-55-5) + 1-[(1,1-dimethylethoxy)carbonyl]-2(S)-(2-methoxyethyl)piperazine (169447-94-3) → 1-[(1,1-dimethylethoxy)carbonyl]-2(S)-(2-methoxyethyl)-4-(1-naphthalenylcarbonyl)piperazine (175357-63-8)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Acylation;	99%

piperidine (110-89-4) + 1-naphthalenecarboxylic acid (86-55-5) → (naphthalen-1-yl)(piperidin-1-yl)methanone (5454-14-8)

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	99%

1-naphthalenecarboxylic acid (86-55-5) + (6RS,11aSR)-6-hydroxymethyl-9-methyl-3-(3-methyl-2,4,5-trimethoxybenzylidene)-2,3,11,11a-tetrahydro-7,8,10-trimethoxy-6H-pyrazino[1,2-b]isoquinoline-1,4-dione → (6RS,11aSR)-6-(1-naphthylcarbonyloxymethyl)-9-methyl-3-(3-methyl-2,4,5-trimethoxybenzylidene)-2,3,11,11a-tetrahydro-7,8,10-trimethoxy-6H-pyrazino[1,2-b]isoquinoline-1,4-dione

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 21h; Inert atmosphere;	99%

ethylbenzene (100-41-4) + 1-naphthalenecarboxylic acid (86-55-5) → 1-phenylethyl 1-naphthoate (1375008-87-9)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In water at 80℃; for 3h;	99%

1-naphthalenecarboxylic acid (86-55-5) + N,0-dimethylhydroxylamine (1117-97-1) → naphthalene-1-(N-methoxy-N-methyl)carboxamide

Conditions	Yield
Stage #1: 1-naphthalenecarboxylic acid; N,0-dimethylhydroxylamine In toluene at 0℃; for 0.166667h; Stage #2: With phosphorus trichloride In toluene at 20 - 60℃; for 0.5h;	99%

1-naphthalenecarboxylic acid (86-55-5) + carbonic acid dimethyl ester (616-38-6) → methyl 1-naphthoate (2459-24-7)

Conditions	Yield
With 25 wt percent zeolite NaY-Bf at 200℃; for 5h; Autoclave; Green chemistry;	99%
With dimanganese decacarbonyl at 180℃; for 1h; Sealed tube;	97%

methanol (67-56-1) + 1-naphthalenecarboxylic acid (86-55-5) → methyl 1-naphthoate (2459-24-7)

Conditions	Yield
With thionyl chloride at 0 - 40℃; for 1h;	98.5%
With oxone at 65℃; for 30h;	92%
With sulfuric acid at 65℃; for 2h;	91%

1-naphthalenecarboxylic acid (86-55-5) + C18H22N4O4 (1219733-88-6) → C29H28N4O5 (1219733-90-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 20h;	98.1%

1-naphthalenecarboxylic acid (86-55-5) + Triethyl orthoacetate (78-39-7) → ethyl 1-naphthoate (3007-97-4)

Conditions	Yield
With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 1.66667h;	98%
In various solvent(s) at 80℃; for 1.66667h;	98%
In toluene at 110℃; for 24h;	89%

1-naphthalenecarboxylic acid (86-55-5) → 1-naphthylcarboxamide (2243-81-4)

Conditions	Yield
With pyridine; ammonium bicarbonate; di-tert-butyl dicarbonate In 1,4-dioxane at 20℃;	98%
Stage #1: 1-naphthalenecarboxylic acid With 1,3,5-trichloro-2,4,6-triazine; potassium carbonate In tetrahydrofuran for 0.0166667h; Milling; Stage #2: With ammonium thiocyanate In tetrahydrofuran for 0.0833333h; Milling;	90%
With ammonium carbonate; ortho-tungstic acid; silver(l) oxide In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 8h;	82.4%

1-naphthalenecarboxylic acid (86-55-5) + potassium phenyltrifluoborate → 2-phenyl-1-naphthalenecarboxylic acid (108981-94-8)

Conditions	Yield
With dipotassium hydrogenphosphate; oxygen; palladium diacetate; p-benzoquinone In tert-butyl alcohol at 100℃; under 22801.5 Torr; for 24h;	98%

1-naphthalenecarboxylic acid (86-55-5) + (3RS,6RS,11aSR)-6-hydroxymethyl-9-methyl-3-(3-methyl-2,4,5-trimethoxy-benzyl)-2,3,11,11a-tetrahydro-7,8,10-trimethoxy-6H-pyrazino[1,2-b]isoquinoline-1,4-dione → (3RS,6RS,11aSR)-6-(1-naphthylcarbonyloxymethyl)-9-methyl-3-(3-methyl-2,4,5-trimethoxybenzyl)-2,3,11,11a-tetrahydro-7,8,10-trimethoxy-6H-pyrazino[1,2-b]isoquinoline-1,4-dione

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 21h; Inert atmosphere;	98%

1-naphthalenecarboxylic acid (86-55-5) + isopropyl bromide (75-26-3) → 1-isopropyl-1,4-dihydronaphthalene-1-carboxylic acid (1202873-28-6)

Conditions	Yield
Stage #1: 1-naphthalenecarboxylic acid With ammonia; lithium In water at -60℃; for 0.5h; Birch reduction; Stage #2: isopropyl bromide With tert-butyl alcohol In water regioselective reaction;	98%
Stage #1: 1-naphthalenecarboxylic acid With ammonia; lithium at -78℃; for 1h; Stage #2: isopropyl bromide at -78℃; for 0.25h;
With ammonia; lithium at -78℃; for 1.25h; Birch Reduction;

1-naphthalenecarboxylic acid (86-55-5) + N-methoxylamine hydrochloride (593-56-6) → N-methoxynaphthalene-1-carboxamide (52288-24-1)

Conditions	Yield
Stage #1: 1-naphthalenecarboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 4h; Under an atmosphere of argon; Stage #2: N-methoxylamine hydrochloride With potassium carbonate In water; ethyl acetate at 0 - 20℃; for 4h;	98%
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃;	75%
Stage #1: 1-naphthalenecarboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3.5h; Stage #2: N-methoxylamine hydrochloride With potassium carbonate In water; ethyl acetate at 20℃; for 20h;

1-naphthalenecarboxylic acid (86-55-5) + cyclohexene (110-83-8) → cyclohex-2-en-1-yl 1-naphthoate (1383677-49-3)

Conditions	Yield
With di-tert-butyl peroxide; C11H23N2(1+)*Br4Fe(1-) In ethyl acetate at 110℃; for 24h;	98%
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In benzene at 80℃; for 8h;	77%

1-naphthalenecarboxylic acid (86-55-5) + 4-((tert-butyldimethylsilyloxy)methyl)phenol (126070-20-0) → 4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl naphthoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 1h; Inert atmosphere; Schlenk technique;	98%

1-naphthalenecarboxylic acid (86-55-5) + 2,2'-dimethyl-[1,1'-biphenyl]iodonium trifluoromethanesulfonate salt → C25H19IO2

Conditions	Yield
With copper diacetate; sodium carbonate; (3aR,3a'R,8aS,8a'S)-2,2'-(propane-2,2-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole) In dichloromethane; water at 30℃; for 12h; enantioselective reaction;	98%

1-naphthalenecarboxylic acid (86-55-5) + 2-phenylethynylphenol (92151-73-0) → 2-(2-phenylacetyl)phenyl 1-naphthoate

Conditions	Yield
Stage #1: 1-naphthalenecarboxylic acid; 2-phenylethynylphenol With bis(1,5-cyclooctadiene)diiridium(I) dichloride In dichloromethane at 20℃; for 1h; Stage #2: With silica gel regioselective reaction;	98%

1-naphthalenecarboxylic acid (86-55-5) + tert-butyl 2-aminobenzylcarbamate (162046-50-6) → tert-butyl N-{[2-(naphthalene-1-amido)phenyl]methyl}carbamate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	98%

Upstream product

• 109-72-8 n-butyllithium 
• 91-20-3 naphthalene 
• 60-29-7 diethyl ether 
• 141-53-7 sodium formate 
• 591-51-5 phenyllithium 
• 1623-99-0 phenyl sodium 
• 71-43-2 benzene 
• 67-56-1 methanol 
• 144782-44-5 diphenylmethyl 1-naphthalenecarboxylate 
• 2459-24-7 methyl 1-naphthoate 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 
• 90-11-9 1-Bromonaphthalene 
• 99747-74-7 1-naphthyl triflate 

Downstream Products

• 13623-57-9 2-naphthalen-1-yl-4,5-dihydro-1H-imidazole 
• 1914-65-4 tetralin-1-carboxylic acid 
• 4242-18-6 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid 
• 7384-42-1 decalin-1-carboxylic acid 
• 16650-52-5 5-chloro-naphthalene-1-carboxylic acid 
• 4537-00-2 8-chloro-1-naphthoic acid 
• 16726-67-3 5-bromo-1-naphthalenecarboxylic acid 
• 4780-79-4 1-naphthalene methanol 
• 3457-41-8 1,2-bis(naphthalen-1-yl)ethane-1,2-dione 
• 39627-76-4 2-hydroxy-1,2-di(naphthalen-1-yl)ethanone 
• 1975-44-6 5-nitro-1-naphthoic acid 
• 2216-13-9 8-nitro-1-naphthalenecarboxylic acid 
• 6240-39-7 (+/-)-(4ar,8ac)-decahydro-[1t]naphthoic acid 
• 134-32-7 1-amino-naphthalene 

Relevant articles and documents

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1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions

Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.