1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-

Base Information

• Chemical Name: 1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-
• CAS No.: 25432-12-6
• Molecular Formula: C₇H₁₄O₄
• Molecular Weight: 162.186
• Mol file: 25432-12-6.mol

Synonyms:2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol;NSC 254136

Chemical Property of 1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-

Chemical Property:

• Boiling Point: 335.9°Cat760mmHg
• Flash Point: 111.9°C
• Density: 1.108g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-

There total 2 articles about 1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl- 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:

dimethyl 2,2-dimethyl-1,3-dioxolane-trans-4,5-dicarboxylate (116499-08-2) → 2,3-O-Isopropyliden-DL-threitol (25432-12-6,50622-09-8,55904-12-6,69460-89-5,73346-74-4,86992-57-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 2h;

DOI:10.1002/adsc.201700057

Reference yield:

→ 2,3-O-Isopropyliden-DL-threitol (25432-12-6,50622-09-8,55904-12-6,69460-89-5,73346-74-4,86992-57-6)

Guidance literature:

Diethyl-2,3-O-isopropyliden-DL-tartrat in Ae., LiAlH4 in Ae. ;

DOI:10.1021/jm00331a004

Reference yield: 90.0%

2,3-O-Isopropyliden-DL-threitol (25432-12-6,50622-09-8,55904-12-6,69460-89-5,73346-74-4,86992-57-6) + 2-(phenylsulfonyl)acetonitrile (7605-28-9) → (3aS,6aS)-5-Benzenesulfonyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-5-carbonitrile

Guidance literature:

With cyanomethylenetributyl-phosphorane; In benzene; at 120 ℃; sealed tube;

DOI:10.1016/0040-4039(96)00318-8

upstream raw materials:

dimethyl 2,2-dimethyl-1,3-dioxolane-trans-4,5-dicarboxylate

Downstream raw materials:

Phenyl-acetic acid (4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

2,3-O-Isopropyliden-DL-threitol-1,4-bis-methansulfonat

Refernces

A new efficient synthetic process for an endothelin receptor antagonist, bosentan monohydrate

10.1021/op400100s

The study presents a novel and efficient synthetic process for bosentan monohydrate, an endothelin receptor antagonist used to treat pulmonary hypertension. The key innovation involves coupling p-tert-butyl-N-(6-chloro-5-(2-methoxy phenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide (7) with (2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanol (14). This method eliminates the formation of critical impurities such as pyrimidinone 8, dimer impurity 9, and N-alkylated impurity 13, which are common in previous synthesis methods. The new process achieves an overall yield of 50-55%, corresponding to an average step yield of 85%, using simple steps and commercially available chemicals. The study also details the optimization of reaction conditions, such as the use of acetonitrile as a solvent and NaOH as a base, and the final purification of bosentan monohydrate using a combination of ethylacetate and methanol. The resulting bosentan monohydrate meets ICH-grade quality standards and exhibits polymorphic stability under various conditions.