ethyl 4-acetoxy-7-chloro-5,8-dimethoxy-naphthalene-2-carboxylate

Base Information

• Chemical Name: ethyl 4-acetoxy-7-chloro-5,8-dimethoxy-naphthalene-2-carboxylate
• CAS No.: 152039-03-7
• Molecular Formula: C17H17ClO6
• Molecular Weight: 352.76628
• Mol file: 152039-03-7.mol

Synonyms:2-Naphthalenecarboxylic acid, 4-(acetyloxy)-7-chloro-5,8-diMethoxy-, ethyl ester

Chemical Property of ethyl 4-acetoxy-7-chloro-5,8-dimethoxy-naphthalene-2-carboxylate

Chemical Property:

• Vapor Pressure: 3.54E-10mmHg at 25°C
• Boiling Point: 501.2°C at 760 mmHg
• Flash Point: 192°C
• PSA: 71.06000
• Density: 1.28g/cm³
• LogP: 3.61240

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 4-acetoxy-7-chloro-5,8-dimethoxy-naphthalene-2-carboxylate

There total 7 articles about ethyl 4-acetoxy-7-chloro-5,8-dimethoxy-naphthalene-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

4-tert-butyl 1-ethyl 2-(diethoxyphosphoryl)succinate (77924-28-8) + 3-chloro-2,5-dimethoxybenzaldehyde (236751-58-9) → ethyl 4-acetoxy-7-chloro-5,8-dimethoxy-2-naphthoate (152039-03-7)

Guidance literature:

4-tert-butyl 1-ethyl 2-(diethoxyphosphoryl)succinate; 3-chloro-2,5-dimethoxybenzaldehyde; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

With trifluoroacetic acid; In water; at 20 ℃; for 0.666667h;

With sodium acetate; acetic anhydride; for 1h; Further stages.; Heating;

DOI:10.1002/chem.200700863

Reference yield:

2-chloro-4-methoxyphenol (18113-03-6) → ethyl 4-acetoxy-7-chloro-5,8-dimethoxy-2-naphthoate (152039-03-7)

Guidance literature:

Multi-step reaction with 6 steps

1: Me₂AlCl / CH₂Cl₂ / 4.5 h / 0 °C

2: K₂CO₃ / acetone / 13 h / Heating

3: 90 percent / MnO₂ / CH₂Cl₂ / 17 h / 40 °C

4: NaH / tetrahydrofuran

5: H₂O; CF₃CO₂H / 1 h

6: NaOAc / 1 h / Heating

With manganese(IV) oxide; water; sodium acetate; dimethylaluminum chloride; sodium hydride; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetone; 1: Alkylation / 2: Methylation / 3: Oxidation / 4: Wittig-Horner reaction / 5: Hydrolysis / 6: Cyclization;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1229::AID-ANIE1229>3.0.CO;2-B

Reference yield:

3-chloro-2,5-dimethoxybenzaldehyde (236751-58-9) → ethyl 4-acetoxy-7-chloro-5,8-dimethoxy-2-naphthoate (152039-03-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / tetrahydrofuran

2: H₂O; CF₃CO₂H / 1 h

3: NaOAc / 1 h / Heating

With water; sodium acetate; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; 1: Wittig-Horner reaction / 2: Hydrolysis / 3: Cyclization;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1229::AID-ANIE1229>3.0.CO;2-B

upstream raw materials:

acetic anhydride

2-chloro-4-methoxyphenol

3-chloro-2,5-dimethoxybenzaldehyde

3-chloro-2,5-dimethoxybenzyl alcohol

Downstream raw materials:

methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-hydroxymethyl-6-methylbenzoate

methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-(methoxymethoxy)methyl-6-methylbenzoate

2-iodo-6-methoxycarbonyl-3-(methoxymethoxy)methyl-5-methylphenyl 7-chloro-4-hydroxy-5,8-dimethoxy-2-naphthoate

7-chloro-4-hydroxy-5,8-dimethoxy-2-naphthoic acid