(S)-(+)-2-Methoxy-2-(1-naphthyl)propionic Acid

Base Information

• Chemical Name: (S)-(+)-2-Methoxy-2-(1-naphthyl)propionic Acid
• CAS No.: 102691-93-0
• Molecular Formula: C14H14 O3
• Molecular Weight: 230.263
• European Community (EC) Number: 672-681-8
• UNII: 68SLX52TK8
• DSSTox Substance ID: DTXSID40431475
• Nikkaji Number: J1.328.331A
• Wikidata: Q27264275
• Mol file: 102691-93-0.mol

Synonyms:102691-93-0;(S)-(+)-2-Methoxy-2-(1-naphthyl)propionic Acid;(s)-2-methoxy-2-(1-naphthyl)propionic acid;(S)-2-METHOXY-2-NAPHTHALEN-1-YL-PROPIONIC ACID;(2S)-2-methoxy-2-naphthalen-1-ylpropanoic acid;2-Methoxy-2-(1-naphthyl)propionic acid, (+)-;UNII-68SLX52TK8;68SLX52TK8;alphaMnp (+)-(S)-form [MI];S-(+)-2-Methoxy-2-(1-naphthyl)propanoic acid;(S)-(-)-2-Methoxy-2-(1-naphthyl)propionic acid;(2S)-2-Methoxy-2-(naphthalen-1-yl)propanoic acid;(S)-2-Methoxy-2-(naphthalen-1-yl)propanoic acid;1-Naphthaleneacetic acid, alpha-methoxy-alpha-methyl- (alphaS)-;(+)-2-Methoxy-2-(1-naphthyl)propionic acid;(S)-(+)-2-Methoxy-2-(1-naphthyl)propionic acid;(alphaS)-alpha-Methoxy-alpha-methyl-1-naphthaleneacetic acid;MFCD03093634;(S)-(+)-alpha-Methoxy-alpha-methyl-1-naphthaleneacetic Acid;(S)-2-Methoxy-2-(1-naphthyl)propionicAcid;SCHEMBL12940368;DTXSID40431475;AMY19650;AKOS015850958;SB30251;CS-11927;.ALPHA.MNP (+)-(S)-FORM [MI];CS-0029560;M1367;(+)-2-methoxy-2-(1-naphthyl)propionic acid;(S)-2-(1-Naphthyl)-2-methoxypropanoic acid;(2S)-2-Methoxy-2-(1-naphthyl)propanoic acid;(S)--Methoxy--methyl-1-naphthaleneacetic acid;s(+)-2-Methoxy-2-(1-naphthyl)propionic acid;A896728;(|AS)-|A-Methoxy-|A-methyl-1-naphthaleneacetic acid;Q27264275;1-Naphthaleneacetic acid, alpha-methoxy-alpha-methyl-, (alphaS)-;1-NAPHTHALENEACETIC ACID, .ALPHA.-METHOXY-.ALPHA.-METHYL- (.ALPHA.S)-

Chemical Property of (S)-(+)-2-Methoxy-2-(1-naphthyl)propionic Acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 110 °C
• Refractive Index: 100 ° (C=1, MeOH)
• Boiling Point: 403.571°C at 760 mmHg
• Flash Point: 154.388°C
• PSA: 46.53000
• Density: 1.204g/cm³
• LogP: 2.78600
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 230.094294304
• Heavy Atom Count: 17
• Complexity: 289

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-(+)-2-Methoxy-2-(1-naphthyl)propionic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC2=CC=CC=C21)(C(=O)O)OC
• Isomeric SMILES: C[C@](C1=CC=CC2=CC=CC=C21)(C(=O)O)OC

Technology Process of (S)-(+)-2-Methoxy-2-(1-naphthyl)propionic Acid

There total 3 articles about (S)-(+)-2-Methoxy-2-(1-naphthyl)propionic Acid 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:

C21H26O4 (1445967-78-1) → C7H14O2 (1445967-80-5) + (S)-2-methoxy-2-(naphthalen-1-yl)propionic acid (102691-93-0)

Guidance literature:

With sodium methylate; In water; at 70 - 80 ℃;

DOI:10.1016/j.tetlet.2013.01.129

Reference yield:

(S)-2-Methoxy-2-naphthalen-1-yl-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (220167-99-7) → (S)-2-methoxy-2-(naphthalen-1-yl)propionic acid (102691-93-0)

Guidance literature:

(S)-2-Methoxy-2-naphthalen-1-yl-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester; With sodium methylate; In methanol;

With sodium hydroxide; In methanol;

DOI:10.1016/S0957-4166(00)00053-7

Reference yield:

rac-2-methoxy-2-(naphthalen-1-yl)propanoic acid (63628-25-1) → (S)-2-methoxy-2-(naphthalen-1-yl)propionic acid (102691-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 49 percent / DCC; DMAP / CH₂Cl₂

2.1: NaOCH₃ / methanol

2.2: aq. NaOH / methanol

With dmap; sodium methylate; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 1.1: Esterification / 2.1: transesterification / 2.2: saponification;

DOI:10.1016/S0957-4166(00)00053-7

upstream raw materials:

(S)-2-Methoxy-2-naphthalen-1-yl-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

rac-2-methoxy-2-(naphthalen-1-yl)propanoic acid

C₂₁H₂₆O₄

Downstream raw materials:

(1S,5S)-3-[(3E)-4,8-dimethylnona-3,7-dienyl]-5-(2,4,5-trimethoxyphenyl)cyclohex-2-enyl (S)-2-methoxy-2-(naphthalen-1-yl)propionate

(1R,5R)-3-[(3E)-4,8-dimethylnona-3,7-dienyl]-5-(2,4,5-trimethoxyphenyl)cyclohex-2-enyl (S)-2-methoxy-2-(naphthalen-1-yl)propionate

Refernces

• 1、 Harada, Nobuyuki,Watanabe, Masataka,Kuwahara, Shunsuke,Sugio, Akinori,Kasai, Yusuke,Ichikawa, Akio. "2-Methoxy-2-(1-naphthyl)propionic acid, a powerful chiral auxiliary for enantioresolution of alcohols and determination of their absolute configurations by the 1H NMR anisotropy method". . p. 1249 - 1253. Retrieved 2007/10/03.