3-(Benzyloxy)-4,5-dimethoxybenzoyl chloride

Base Information

• Chemical Name: 3-(Benzyloxy)-4,5-dimethoxybenzoyl chloride
• CAS No.: 5065-11-2
• Molecular Formula: C16H15ClO4
• Molecular Weight: 306.746
• DSSTox Substance ID: DTXSID30501555
• Wikidata: Q82354011
• Mol file: 5065-11-2.mol

Synonyms:3-(Benzyloxy)-4,5-dimethoxybenzoyl chloride;5065-11-2;DTXSID30501555;5-benzyloxy-3,4-dimethoxybenzoyl chloride

Chemical Property of 3-(Benzyloxy)-4,5-dimethoxybenzoyl chloride

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 306.0658866
• Heavy Atom Count: 21
• Complexity: 330

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C(=CC(=C1)C(=O)Cl)OCC2=CC=CC=C2)OC

Technology Process of 3-(Benzyloxy)-4,5-dimethoxybenzoyl chloride

There total 2 articles about 3-(Benzyloxy)-4,5-dimethoxybenzoyl 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:

3-(benzyloxy)-4,5-dimethoxybenzoic acid (5651-55-8) → 3-benzyloxy-4,5-dimethoxybenzoyl chloride (5065-11-2)

Guidance literature:

With oxalyl dichloride; In benzene;

DOI:10.1016/S0040-4020(01)96977-7

Reference yield:

→ 3-benzyloxy-4,5-dimethoxybenzoyl chloride (5065-11-2)

Guidance literature:

Kochen d. Saeure mit SOCl2;

Reference yield:

3-benzyloxy-4,5-dimethoxybenzoyl chloride (5065-11-2) → (+/-)-trans-2,5-bis[4,5-dimethoxy-3-[3-(4-methylthiazol-5-yl)propoxy]phenyl]tetrahydrofuran

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-BuLi / 1.) Et₂O, from -65 to 0 deg C, 2.) Et₂O, RT, 2 h

2: 47 percent / Et₃N, NaI / acetonitrile / 0.25 h / Ambient temperature

3: 1.) MeLi, 2.) Cu(OSO₂CF₃)2 / 1.) THF, -70 deg C, 10 min, 2.) THF, isobutyronitrile, from -70 deg C to RT, 2.5 h

4: NaBH₄ / ethanol / 1.33 h / 70 °C

5: trifluoroacetic acid / CHCl₃ / 1.5 h / Ambient temperature

6: 66 percent / H₂ / 5percent Pd/C / ethanol / 760 Torr / Ambient temperature

7: K₂CO₃ / dimethylformamide / 5 h / 80 °C

With sodium tetrahydroborate; n-butyllithium; methyllithium; hydrogen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In ethanol; chloroform; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0223-5234(96)89161-6

upstream raw materials:

3-(benzyloxy)-4,5-dimethoxybenzoic acid

Downstream raw materials:

2-(3'-benzyloxy-4',5'-dimethoxy)benzoyloxy-3,4,6-trimethoxyacetophenone

3-Benzyloxy-4,5-dimethoxyacetophenone

(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-yl 3''-benzyloxy-4'',5''-dimethoxybenzoate

(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4'-bis(benzyloxy)-phenyl]chroman-3-yl 3''-benzyloxy-4'',5''-dimethoxybenzoate

Refernces

• 1、 Zhang, Liang,Zhang, Wei-Ge,Ma, En-Long,Wu, Lan,Bao, Kai,Wang, Xiao-Long,Wang, Yu-Ling,Song, Hong-Rui. "Synthesis and antiproliferative in-vitro activity of natural flavans and related compounds". . p. 650 - 655. Retrieved 2008/12/21.
• 2、 Smith,Blackwell,Demaine,Garland,Hodson,Hyde,Parke,Rose,Sawyer,Tilling. "Synthesis and PAF antagonist activity of some 2,5-diaryltetrahydrofurans incorporating PAF-like functional groups". . p. 347 - 358. Retrieved 2007/10/03.