3,5-Dibenzyloxyphenol

Base Information

• Chemical Name: 3,5-Dibenzyloxyphenol
• CAS No.: 63604-98-8
• Molecular Formula: C20H18O3
• Molecular Weight: 306.361
• DSSTox Substance ID: DTXSID70473868
• Nikkaji Number: J1.618.605H
• Mol file: 63604-98-8.mol

Synonyms:3,5-dibenzyloxyphenol;63604-98-8;3,5-bis(phenylmethoxy)phenol;Phenol, 3,5-bis(phenylmethoxy)-;3,5-bis(benzyloxy)phenol;phloroglucinol dibenzyl ether;SCHEMBL1834526;DTXSID70473868;FEQJBICMACXNHS-UHFFFAOYSA-N;3,?5-?Bis(phenylmethoxy)?phenol

Chemical Property of 3,5-Dibenzyloxyphenol

Chemical Property:

• Melting Point: 94 °C
• Boiling Point: 505.1±40.0 °C(Predicted)
• PSA: 38.69000
• Density: 1.190±0.06 g/cm3(Predicted)
• LogP: 4.55020
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 306.125594432
• Heavy Atom Count: 23
• Complexity: 291

Purity/Quality:

99% ^*data from raw suppliers

3,?5-?Bis(phenylmethoxy)?phenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC(=CC(=C2)O)OCC3=CC=CC=C3
• Uses: 3,?5-?Bis(phenylmethoxy)?phenol is used as a reagent for Friedel-?Crafts propargylic alkylation for phenol structures.1

Technology Process of 3,5-Dibenzyloxyphenol

There total 18 articles about 3,5-Dibenzyloxyphenol 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: 95.0%

phloroglucinol dibenzyl ether monobenzenesulfonate (78596-73-3) → 1,3-dibenzylphloroglucinol (63604-98-8)

Guidance literature:

With potassium hydroxide; In methanol; water; for 18h; Heating;

DOI:10.1021/ja00402a039

Reference yield: 93.0%

1,3,5-tri-O-benzylphloroglucinol (59434-20-7) → 1,3-dibenzylphloroglucinol (63604-98-8)

Guidance literature:

With hydrogen; sodium methylate; palladium on activated charcoal; In 1,4-dioxane; methanol;

DOI:10.1021/ol0528585

Reference yield: 64.0%

1,3,5-tri-O-benzylphloroglucinol (59434-20-7) → 2-benzyl-3,5-bis(benzyloxy)phenol (850307-78-7) + 1,3-dibenzylphloroglucinol (63604-98-8)

Guidance literature:

With n-butanethiol; sodium hydride; In N,N-dimethyl-formamide; at 150 ℃; for 1.5h;

DOI:10.1016/j.bmc.2004.12.056

upstream raw materials:

methyl 2,4-dibenzyloxy-6-hydroxybenzoate

3,5-dihydroxyphenol

benzyl chloride

phloroglucinol dibenzyl ether monobenzenesulfonate

Downstream raw materials:

(E)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4,5-tris(benzyloxy)phenyl]-propene

C₈₁H₈₄O₁₂

(E)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-(4-benzyloxyphenyl)propene

3,4,5-Tris-dodecyloxy-benzoic acid 4-(3,5-dihydroxy-phenoxycarbonyl)-phenyl ester

Refernces

Synthesis of 1-[3,5-bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,4, 6-hihydroxyphenyl]ethanone : An intermediate of potential usefulness for synthesis of bis-C-glucosyl flavonoids

10.1016/S0008-6215(96)00280-7

The research aimed to synthesize 1-[3,5-bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]ethanone, an intermediate compound that is potentially useful for the synthesis of bis-C-glucosyl flavonoids. The study focused on the bis-glycosylation of 3,5-dibenzyloxyphenol with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride in a two-step sequence, resulting in the bis-glucosylated product, 3,5-dibenzyloxy-2,6-bis-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)phenol. The subsequent steps involved hydrogenolytic debenzylation and acetylation to yield the undeca-O-acetyl derivative, which was then subjected to Friedel-Crafts acylation with borontrifluoride-acetic acid to obtain the 4-C-acetyl target compound. The research concluded that this methodology is now available for the synthesis of bis-C-glycosyl compounds, and further syntheses of bis-C-glycosyl flavonoids are in progress.