3,5-Bis(benzyloxy)benzoyl chloride

Base Information

• Chemical Name: 3,5-Bis(benzyloxy)benzoyl chloride
• CAS No.: 28917-44-4
• Molecular Formula: C21H17ClO3
• Molecular Weight: 352.817
• DSSTox Substance ID: DTXSID20445550
• Nikkaji Number: J1.686.798E
• Wikidata: Q82264004
• Mol file: 28917-44-4.mol

Synonyms:3,5-bis(benzyloxy)benzoyl chloride;28917-44-4;3,5-dibenzyloxybenzoyl chloride;Benzoyl chloride, 3,5-bis(phenylmethoxy)-;SCHEMBL1795022;3,5-Dibenzyloxy-benzoyl-chloride;DTXSID20445550;GWIBCCZNAYLLCD-UHFFFAOYSA-N;3,5-bis(benzyloxy) benzoyl chloride;3,5-bis(benzyloxy)benzoic acid chloride

Chemical Property of 3,5-Bis(benzyloxy)benzoyl chloride

Chemical Property:

• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 352.0866221
• Heavy Atom Count: 25
• Complexity: 372

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC(=CC(=C2)C(=O)Cl)OCC3=CC=CC=C3

Technology Process of 3,5-Bis(benzyloxy)benzoyl chloride

There total 13 articles about 3,5-Bis(benzyloxy)benzoyl chloride 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: 100.0%

3,5-dibenzyloxybenzoic acid (28917-43-3) → 3,5-dibenzyloxylbenzoyl chloride (28917-44-4)

Guidance literature:

With thionyl chloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 50 ℃; for 4h;

DOI:10.1007/s11172-015-1203-0

Reference yield:

methyl 3,5-bis(benzyloxy)benzoate (58605-10-0) → 3,5-dibenzyloxylbenzoyl chloride (28917-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1: KOH / ethanol

2: SOCl₂ / 20 h / 85 °C

With potassium hydroxide; thionyl chloride; In ethanol;

DOI:10.1002/1521-3765(20020118)8:2<467::AID-CHEM467>3.0.CO;2-1

Reference yield:

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → 3,5-dibenzyloxylbenzoyl chloride (28917-44-4)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / acetone / 20 h / Heating

2: 90 percent / 10percent aq. NaOH / acetone / 2 h / Heating

3: 65 percent / SOCl₂ / benzene / 5 h / Heating

With sodium hydroxide; thionyl chloride; potassium carbonate; In acetone; benzene;

DOI:10.1002/(SICI)1099-1344(199604)38:4<309::AID-JLCR775>3.0.CO;2-5

upstream raw materials:

3,5-dibenzyloxybenzoic acid

methyl 3,5-bis(benzyloxy)benzoate

3,5-Dihydroxybenzoic acid

(3,5-di-benzyloxy)benzoic acid benzyl ester

Downstream raw materials:

3,5-dibenzyloxyphenylacetic acid

(S)-4-Benzyl-3-[2-(3,5-bis-benzyloxy-phenyl)-acetyl]-oxazolidin-2-one

(S)-Alloc-Dhpg(OBn)2-OH

(S)-3-[(S)-2-Azido-2-(3,5-bis-benzyloxy-phenyl)-acetyl]-4-benzyl-oxazolidin-2-one

Refernces

• 1、 Fuse, Shinichiro,Otake, Yuma,Mifune, Yuto,Tanaka, Hiroshi. "A facile preparation of α-aryl carboxylic acid via one-flow arndt-eistert synthesis". . p. 1657 - 1661. Retrieved 2015/11/10.
• 2、 Cheng, Yung-Yi,Liu, Chin-Yu,Tsai, Meng-Tung,Lin, Hui-Yi,Yang, Jai-Sing,Wu, Tian-Shung,Kuo, Sheng-Chu,Huang, Li-Jiau,Lee, Kuo-Hsiung. "Design, synthesis, and mechanism of action of 2-(3-hydroxy-5-methoxyphenyl) -6-pyrrolidinylquinolin-4-one as a potent anticancer lead". . p. 5223 - 5227. Retrieved 2013/09/12.