13057-65-3

Basic information

• Product Name: beta-(2-methoxyphenoxy)lactic acid
• Synonyms: beta-(2-methoxyphenoxy)lactic acid;2-Hydroxy-3-(2-methoxyphenoxy)propanoic acid
• CAS NO: 13057-65-3
• Molecular Formula: C₁₀H₁₂O₅
• Molecular Weight: 212.2
• Mol File: 13057-65-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 355.8°Cat760mmHg
• Flash Point: 139.8°C
• Appearance: /
• Density: 1.302 g/cm³
• Vapor Pressure: 1.12E-05mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: beta-(2-methoxyphenoxy)lactic acid(CAS DataBase Reference)
• NIST Chemistry Reference: beta-(2-methoxyphenoxy)lactic acid(13057-65-3)
• EPA Substance Registry System: beta-(2-methoxyphenoxy)lactic acid(13057-65-3)

Safety Data

• Hazardous Substances Data: 13057-65-3(Hazardous Substances Data)

Usage

Uses

3-(2-Methoxyphenoxy) Lactic Acid is a metabolite of the Guaifenesin (G810500), a centrally acting muscle relaxant with expectorant properties.

InChI:InChI=1/C10H12O5/c1-14-8-4-2-3-5-9(8)15-6-7(11)10(12)13/h2-5,7,11H,6H2,1H3,(H,12,13)

Synthetic route

sodium 2-methoxyphenolate (13052-77-2) + 3-chloro-2-hydroxypropanoic acid (1713-85-5) → CVT-4786 (13057-65-3)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Reflux;	74%

guaifenesin (93-14-1) → CVT-4786 (13057-65-3)

Conditions	Yield
Stage #1: guaifenesin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; toluene at 25℃; for 0.0833333h; pH=6.8; Stage #2: With sodium hypochlorite; sodium chlorite In aq. phosphate buffer; water; toluene at 50℃; for 24h; pH=6.8;	73%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite In water; acetonitrile at 35℃; aq. phosphate buffer; chemoselective reaction;	37.4%

guaifenesin (93-14-1) → (2-methoxyphenoxy)acetic acid (1878-85-9) + CVT-4786 (13057-65-3)

Conditions	Yield
Stage #1: guaifenesin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; toluene at 25℃; pH=6.8; Stage #2: With sodium hypochlorite; sodium chlorite In aq. phosphate buffer; toluene at 50℃; for 24h; chemoselective reaction;	A 10 %Spectr. B 73%

2-methoxy-phenol (90-05-1) → CVT-4786 (13057-65-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran; mineral oil 2: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Reflux View Scheme

diazomethane (186581-53-3, 908094-01-9) + CVT-4786 (13057-65-3) → C11H14O5

Conditions	Yield
In methanol; diethyl ether	n/a

Upstream product

• 93-14-1 guaifenesin 
• 13052-77-2 sodium 2-methoxyphenolate 
• 1713-85-5 3-chloro-2-hydroxypropanoic acid 
• 90-05-1 2-methoxy-phenol 

Relevant articles and documents

PRODUCTION METHOD OF α-HYDROXYCARBOXYLIC ACID

PROBLEM TO BE SOLVED: To provide an efficient production method of an α-hydroxycarboxylic acid in a mild condition, and to provide a production method of a biodegradable plastic from a raw material containing the α-hydroxycarboxylic acid. SOLUTION: In a synthesis method of an α-hydroxycarboxylic acid, which is a production method of the α-hydroxycarboxylic acid by oxidizing a 1,2-diol compound in a reaction system using a nitroxy radical including a skeleton represented by formula(1), water, and an organic solvent, the organic solvent is a compound unmixable with water (R1-R4 are respectively and independently 1-6C hydrocarbon groups). In the synthesis method of the α-hydroxycarboxylic acid, the reaction system has a pH value of 1.0-8.0, and includes a phosphate buffer solution or an acetate buffer solution, and at least one selected from a hypohalite and a halite is added to the reaction system, and further at least one selected from a tetraalkylammonium salt and a fatty acid is added thereto. COPYRIGHT: (C)2016,JPOandINPIT

Synthesis of enantiomerically pure 3-aryloxy-2-hydroxypropanoic acids, intermediate products in the synthesis of cis-4-Aminochroman-3-ols

Oxidation of accessible (R)-3-chloropropane-1,2-diol to (R)-3-chloro-2-hydroxypropanoic acid and subsequent reaction of the latter with ortho-substituted sodium phenoxide gave a number of enantiomerically pure 3-aryloxy-2-hydroxypropanoic acid which are intermediate products in the synthesis of nonracemic 4-aminochroman-3-ols.