Methyl 2-(naphthalen-1-yl)-2-oxoacetate

Base Information

• Chemical Name: Methyl 2-(naphthalen-1-yl)-2-oxoacetate
• CAS No.: 16738-12-8
• Molecular Formula: C13H10O3
• Molecular Weight: 214.221
• DSSTox Substance ID: DTXSID201300112
• Nikkaji Number: J462.952C
• Mol file: 16738-12-8.mol

Synonyms:Methyl 2-(naphthalen-1-yl)-2-oxoacetate;16738-12-8;methyl 2-naphthalen-1-yl-2-oxoacetate;1-Naphthaleneacetic acid, alpha-oxo-, methyl ester;SCHEMBL7640335;SZAFHPVKHPLRRD-UHFFFAOYSA-N;DTXSID201300112;methyl 2-oxo-2-(1-naphthyl)acetate;Methyl alpha-oxo-1-naphthaleneacetate;Methyl2-(naphthalen-1-yl)-2-oxoacetate;CS-0447811;F80732

Chemical Property of Methyl 2-(naphthalen-1-yl)-2-oxoacetate

Chemical Property:

• PSA: 43.37000
• LogP: 2.19550
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 214.062994177
• Heavy Atom Count: 16
• Complexity: 285

Purity/Quality:

95%-98% ^*data from raw suppliers

Methyl2-(naphthalen-1-yl)-2-oxoacetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=O)C1=CC=CC2=CC=CC=C21

Technology Process of Methyl 2-(naphthalen-1-yl)-2-oxoacetate

There total 12 articles about Methyl 2-(naphthalen-1-yl)-2-oxoacetate 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: 90.0%

methyl 2-diazo-2-(naphthalen-1-yl)acetate (370561-84-5) → methyl α-oxo-1-naphthaleneacetate (16738-12-8)

Guidance literature:

With water; diethylazodicarboxylate; dirhodium tetraacetate; In toluene; for 4h; Heating;

DOI:10.1055/s-2006-950412

Reference yield: 74.0%

methanol (67-56-1) + 4,4,4-trifluoro-3-hydroxy-1-(naphthalen-1-yl)but-2-en-1-one → methyl α-oxo-1-naphthaleneacetate (16738-12-8)

Guidance literature:

With tert.-butylhydroperoxide; iodine; sodium carbonate; In 1,2-dichloro-ethane; at 60 ℃; for 7h;

DOI:10.1055/s-0036-1588833

Reference yield: 71.0%

methanol (67-56-1) + 1'-naphthacetophenone (941-98-0) → methyl α-oxo-1-naphthaleneacetate (16738-12-8)

Guidance literature:

1'-naphthacetophenone; With pyridine; selenium(IV) oxide; at 100 ℃; for 15h; Inert atmosphere;

methanol; With thionyl chloride; at 20 ℃; Cooling with ice; Molecular sieve;

With perchloric acid; water; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2009.09.076

upstream raw materials:

methyl 1-naphthylacetate

(+/-)-Methyl α-methoxy-α-(1-naphthyl)acetate

methyl 2-diazo-2-(naphthalen-1-yl)acetate

methyl 2-hydroxy-2-(naphthalen-1-yl)acetate

Downstream raw materials:

naphth-1-yl acetic acid

Refernces

• 1、 Fan, Zhengning,Yi, Yaping,Chen, Shenhao,Xi, Chanjuan. "Visible-Light-Induced Catalyst-Free Carboxylation of Acylsilanes with Carbon Dioxide". supporting information. p. 2303 - 2307. Retrieved 2021/04/05.
• 2、 -. "Preparation method of alpha-naphthylacetic acid". Paragraph 0009; 0023; 0027. . Retrieved 2020/08/22.