3-Chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid

Base Information

• Chemical Name: 3-Chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid
• CAS No.: 101536-78-1
• Molecular Formula: C10H11ClO4
• Molecular Weight: 230.648
• DSSTox Substance ID: DTXSID20540635
• Wikidata: Q82416698
• Mol file: 101536-78-1.mol

Synonyms:101536-78-1;3-Chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid;SCHEMBL24684796;DTXSID20540635;3-Chloro-5-ethyl-6-hydroxy-2-methoxybenzoicacid

Chemical Property of 3-Chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 230.0345865
• Heavy Atom Count: 15
• Complexity: 234

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1=CC(=C(C(=C1O)C(=O)O)OC)Cl

Technology Process of 3-Chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid

There total 2 articles about 3-Chloro-5-ethyl-6-hydroxy-2-methoxybenzoic 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: 83.0%

3-ethyl-6-methoxysalicilic acid (98527-27-6) → 3-chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid (101536-78-1)

Guidance literature:

With sulfuryl dichloride; In chloroform; for 4h; Ambient temperature;

Reference yield:

2,6-dimethoxy-3-ethylbenzoic acid (96897-97-1) → 3-chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid (101536-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr/HOAc / H₂O / 1 h / 35 °C

2: 83 percent / sulphuryl chloride / CHCl₃ / 4 h / Ambient temperature

With sulfuryl dichloride; hydrogen bromide; acetic acid; In chloroform; water;

Reference yield: 63.0%

tert-butyl (2S,4R)-2-(aminomethyl)-4-(4-((2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy)butoxy)pyrrolidine-1-carboxylate + 3-chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid (101536-78-1) → tert-butyl (2S,4R)-2-((3-chloro-5-ethyl-6-hydroxy-2-methoxybenzamido)methyl)-4-(4-((2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy)butoxy)pyrrolidine-1-carboxylate

Guidance literature:

3-chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid; With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); In chloroform; at 20 ℃; for 0.166667h;

tert-butyl (2S,4R)-2-(aminomethyl)-4-(4-((2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy)butoxy)pyrrolidine-1-carboxylate; In chloroform; at 20 ℃;

DOI:10.1021/acs.jmedchem.1c01353

upstream raw materials:

3-ethyl-6-methoxysalicilic acid

2,6-dimethoxy-3-ethylbenzoic acid

Downstream raw materials:

Eticlopride hydrochloride

(2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-tert-butyldimethylsilyloxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide

3-chloro-5-ethyl-6-hydroxy-2-methoxybenzoyl chloride

(S)-(-)-5-chloro-3-ethyl-N-<<1-(2'-hydroxyethyl)-2-pyrrolidinyl>methyl>-6-methoxysalicylamide