3,5-Bis(benzyloxy)-2-hydroxybenzaldehyde

Base Information

• Chemical Name: 3,5-Bis(benzyloxy)-2-hydroxybenzaldehyde
• CAS No.: 85565-92-0
• Molecular Formula: C₂₁H₁₈O₄
• Molecular Weight: 334.372
• Mol file: 85565-92-0.mol

Synonyms:3,5-Bis(benzyloxy)-2-hydroxybenzaldehyde

Chemical Property of 3,5-Bis(benzyloxy)-2-hydroxybenzaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-Bis(benzyloxy)-2-hydroxybenzaldehyde

There total 8 articles about 3,5-Bis(benzyloxy)-2-hydroxybenzaldehyde 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: 55.0%

2,4-bis(benzyloxy)phenol (6195-80-8) + hexamethylenetetramine (100-97-0) → 3,5-Bis(benzyloxy)-2-hydroxybenzaldehyde (85565-92-0)

Guidance literature:

hexamethylenetetramine; With acetic acid; for 0.0833333h;

2,4-bis(benzyloxy)phenol; With acetic acid; In N,N-dimethyl-formamide; for 3h; Reflux;

DOI:10.1021/acs.jnatprod.6b00861

Reference yield:

2-bromo-3,5-bis(benzyloxy)benzaldehyde (85565-94-2) → 3,5-dibenzyloxybenzaldehyde (14615-72-6) + 3,5-Bis(benzyloxy)-2-hydroxybenzaldehyde (85565-92-0)

Guidance literature:

With n-butyllithium; nitrobenzene; Yield given. Multistep reaction; 1.) THF, hexane, -75 deg C, 50 min.; 2.) -75 deg C, 4h, -> room temp.;

DOI:10.1021/jo00160a001

Reference yield:

2,4-dibenzyloxybenzaldehyde (13246-46-3) → 3,5-Bis(benzyloxy)-2-hydroxybenzaldehyde (85565-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dihydrogen peroxide; sulfuric acid / methanol; water / 2 h / 20 °C

2.1: acetic acid / 0.08 h

2.2: 3 h / Reflux

With sulfuric acid; dihydrogen peroxide; acetic acid; In methanol; water;

DOI:10.1021/acs.jnatprod.6b00861

upstream raw materials:

2-bromo-3,5-bis(benzyloxy)benzaldehyde

3,5-Dihydroxybenzoic acid

3,5-dibenzyloxybenzyl alcohol

benzyl chloride

Downstream raw materials:

2,4-dihydroxy-6-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl-β-D-glucopyranoside

Refernces

• 1、 Sinhababu, Achintya K.,Borchardt, Ronald T.. "Aromatic Hydroxylation. Hydroxybenzaldehydes from Bromobenzaldehydes via Reaction of in Situ Generated, Lithiated α-Morpholinobenzyl Alkoxides with Nitrobenzene". . p. 1941 - 1944. Retrieved 2007/10/02.