[4-(Acetyloxy)-1,3-dioxolan-2-YL]methyl benzoate

Base Information

• Chemical Name: [4-(Acetyloxy)-1,3-dioxolan-2-YL]methyl benzoate
• CAS No.: 145354-82-1
• Molecular Formula: C₁₃H₁₄O₆
• Molecular Weight: 266.251
• DSSTox Substance ID: DTXSID90431501
• Mol file: 145354-82-1.mol

Synonyms:145354-82-1;[4-(ACETYLOXY)-1,3-DIOXOLAN-2-YL]METHYL BENZOATE;(4-acetyloxy-1,3-dioxolan-2-yl)methyl Benzoate;BENZOIC ACID (S)-4-ACETOXY-[1,3]DIOXOLAN-2-YLMETHYL ESTER;SCHEMBL132805;DTXSID90431501

Chemical Property of [4-(Acetyloxy)-1,3-dioxolan-2-YL]methyl benzoate

Chemical Property:

• Boiling Point: 365.7±37.0 °C(Predicted)
• PSA: 71.06000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 1.10550
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 266.07903816
• Heavy Atom Count: 19
• Complexity: 323

Purity/Quality:

(S)-4-ACETOXY-[1,3]DIOXOLAN-2-YL BENZOIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1COC(O1)COC(=O)C2=CC=CC=C2

Technology Process of [4-(Acetyloxy)-1,3-dioxolan-2-YL]methyl benzoate

There total 7 articles about [4-(Acetyloxy)-1,3-dioxolan-2-YL]methyl benzoate 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:

lead(IV) tetraacetate (546-67-8) + (2S,4S)-2-Benzoyloxymethyl-[1,3]dioxolane-4-carboxylic acid (145354-81-0) → (2S,4RS)-4-acetoxy-2-<(benzoyloxy)methyl>dioxolane (214273-21-9,145354-82-1)

Guidance literature:

With pyridine; In tetrahydrofuran; for 0.75h;

DOI:10.1021/jm00057a001

Reference yield:

benzoyl chloride (98-88-4) → (2S,4RS)-4-acetoxy-2-<(benzoyloxy)methyl>dioxolane (214273-21-9,145354-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / Ambient temperature

2: p-TsOH / methanol / Ambient temperature

3: NaIO₄ / RuO₂ / acetonitrile; CCl₄; H₂O / Ambient temperature

4: tetrahydrofuran / Ambient temperature

With pyridine; sodium periodate; toluene-4-sulfonic acid; ruthenium(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)60890-0

Reference yield:

Benzoic acid (2S,4S)-4-((R)-1,2-dihydroxy-ethyl)-[1,3]dioxolan-2-ylmethyl ester (145354-80-9) → (2S,4RS)-4-acetoxy-2-<(benzoyloxy)methyl>dioxolane (214273-21-9,145354-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaIO₄ / RuO₂ / acetonitrile; CCl₄; H₂O / Ambient temperature

2: tetrahydrofuran / Ambient temperature

With sodium periodate; ruthenium(IV) oxide; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)60890-0

upstream raw materials:

lead(IV) tetraacetate

(2S,4S)-2-Benzoyloxymethyl-[1,3]dioxolane-4-carboxylic acid

benzoyl chloride

(+)-(1'S,2S,4S)-4-(1,2-dihydroxyethyl)-2-<(benzoyloxy)methyl>dioxolane

Downstream raw materials:

benzoic acid 4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester

benzoic acid 4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethyl ester