4-[(Allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: 4-[(Allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
• CAS No.: 4421-23-2
• Molecular Formula: C₉H₁₆O₃
• Molecular Weight: 172.224
• Hs Code.: 2932990090
• DSSTox Substance ID: DTXSID30381632
• Nikkaji Number: J1.598.007I
• Mol file: 4421-23-2.mol

Synonyms:4421-23-2;4-[(Allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane;2,2-dimethyl-4-(prop-2-enoxymethyl)-1,3-dioxolane;1,3-Dioxolane, 2,2-dimethyl-4-[(2-propenyloxy)methyl]-;Allyl solketyl ether;4-[Allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane;SCHEMBL46416;Glycerol acetonide allyl ether;DTXSID30381632;KDHJNSAZMYPQKD-UHFFFAOYSA-N;AKOS015842124;1,2-Isopropylideneglycerin allyl ether;1-O,2-O-Isopropylidene-3-O-allylglycerol;FT-0692388;4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane;4-(allyloxymethyl)-2,2-dimethyl-1,3-dioxolane;2,2-Dimethyl-4-[(2-propen-1-yloxy)methyl]-1,3-dioxolane;2,2-Dimethyl-4-{[(prop-2-en-1-yl)oxy]methyl}-1,3-dioxolane

Chemical Property of 4-[(Allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

Chemical Property:

• Boiling Point: 87 °C(Press: 22 Torr)
• PSA: 27.69000
• Density: 0.9870 g/cm3
• LogP: 1.34050
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 172.109944368
• Heavy Atom Count: 12
• Complexity: 154

Purity/Quality:

95% ^*data from raw suppliers

4-[(Allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)COCC=C)C

Technology Process of 4-[(Allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

There total 6 articles about 4-[(Allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane 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: 100.0%

allyl bromide (106-95-6) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0) → 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane (4421-23-2,18657-14-2,56083-15-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -10 - 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2012.06.059

Reference yield: 98.0%

Allyl glycidyl ether (106-92-3,25639-25-2,90907-93-0) + acetone (67-64-1) → 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane (4421-23-2,18657-14-2,56083-15-9)

Guidance literature:

With 12-molybdo phosphoric acid n-hydrate; at 20 ℃; for 0.0166667h; neat (no solvent);

DOI:10.1080/10426500801960554

Reference yield: 95.0%

3-chloroprop-1-ene (107-05-1) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0) → 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane (4421-23-2,18657-14-2,56083-15-9)

Guidance literature:

With sodium hydroxide; In toluene; at 30 ℃; for 6h;

DOI:10.1134/S1070427215100079

upstream raw materials:

allyl bromide

4-benzoyloxymethyl-2,2-dimethyl-[1,3]dioxolane

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol

Allyl glycidyl ether

Downstream raw materials:

2-(allyloxy)acetaldehyde

3-allyloxy-1,2-propanediol

Refernces

• 1、 Raskil’dina,Borisova, Yu. G.,Zlotskii. "Condensation of 1,2,4-Butanetriol with Carbonyl Compounds and Reactions of Hydroxyalkyl-1,3-dioxacyclanes". . p. 1601 - 1605. Retrieved 2018/11/10.
• 2、 Raskil'Dina,Valiev,Sultanova,Zlotskii. "Selective functionalization of the primary hydroxy group in triols". . p. 1599 - 1604. Retrieved 2016/02/18.