{5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol

Base Information

• Chemical Name: {5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol
• CAS No.: 852520-72-0
• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.39
• Mol file: 852520-72-0.mol

Synonyms:{5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol

Chemical Property of {5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol

There total 6 articles about {5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol 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: 96.0%

5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (852520-71-9) → {5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol (852520-72-0)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at 0 - 20 ℃; for 2h;

DOI:10.1021/jo050193e

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → {5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol (852520-72-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / sodium hydride; tetra(n-butyl)ammonium iodide / dimethylformamide / 1 h / 0 °C

2: 95 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

3: 89 percent / benzene / 6 h / Heating

4: 96 percent / potassium ferricyanide; potassium carbonate; osmium tetroxide / (DHQD)2PHAL; methanesulfonamide / 2-methyl-propan-2-ol; H₂O; toluene / 24 h / 0 °C

5: 95 percent / p-TSA / CH₂Cl₂ / 20 °C

6: 96 percent / DIBAL-H / CH₂Cl₂; toluene / 2 h / 0 - 20 °C

With osmium(VIII) oxide; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 2: Swern oxidation / 3: Wittig olefination / 4: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo050193e

Reference yield:

4-((4-methoxybenzyl)oxy)butanal (119649-27-3) → {5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol (852520-72-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / benzene / 6 h / Heating

2: 96 percent / potassium ferricyanide; potassium carbonate; osmium tetroxide / (DHQD)2PHAL; methanesulfonamide / 2-methyl-propan-2-ol; H₂O; toluene / 24 h / 0 °C

3: 95 percent / p-TSA / CH₂Cl₂ / 20 °C

4: 96 percent / DIBAL-H / CH₂Cl₂; toluene / 2 h / 0 - 20 °C

With osmium(VIII) oxide; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In dichloromethane; water; toluene; tert-butyl alcohol; benzene; 1: Wittig olefination / 2: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo050193e

upstream raw materials:

5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

2,3-dihydroxy-6-(4-methoxybenzyloxy)-hexanoic acid ethyl ester

p-Methoxybenzyl bromide

4-(p-methoxybenzyloxy)butan-1-ol

Downstream raw materials:

(4S,5R)-5-[3-(4-Methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

tert-butyl-[4-{5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-(1-methoxymethoxyheptyl)-but-3-ynyloxy]-dimethylsilane

1-{5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methoxymethoxy-undec-1-yn-4-ol

4-(2,2-dibromovinyl)-5-[3-(4-methoxybenzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolane