Orthobenzoic acid, cyclic ester with 2-(hydroxymethyl)-2-methyl-1,3-propanediol

Base Information

• Chemical Name: Orthobenzoic acid, cyclic ester with 2-(hydroxymethyl)-2-methyl-1,3-propanediol
• CAS No.: 70637-00-2
• Molecular Formula: C12H14 O3
• Molecular Weight: 206.241
• DSSTox Substance ID: DTXSID30220916
• Nikkaji Number: J694.891J
• Wikidata: Q83098438
• Mol file: 70637-00-2.mol

Synonyms:70637-00-2;BRN 4439813;Orthobenzoic acid, cyclic ester with 2-(hydroxymethyl)-2-methyl-1,3-propanediol;2,6,7-Trioxabicyclo(2.2.2)octane, 4-methyl-1-phenyl-;4-METHYL-1-PHENYL-2,6,7-TRIOXABICYCLO[2.2.2]OCTANE;2,6,7-Trioxabicyclo[2.2.2]octane, 4-methyl-1-phenyl-;DTXSID30220916;LS-98454;1-Phenyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane;4-Methyl-1-phenyl-2,6,7-trioxa-bicyclo[2.2.2]octane

Chemical Property of Orthobenzoic acid, cyclic ester with 2-(hydroxymethyl)-2-methyl-1,3-propanediol

Chemical Property:

• Vapor Pressure: 0.00788mmHg at 25°C
• Boiling Point: 276.9°C at 760 mmHg
• Flash Point: 91.5°C
• PSA: 27.69000
• Density: 1.214g/cm³
• LogP: 1.88020
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 206.094294304
• Heavy Atom Count: 15
• Complexity: 221

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12COC(OC1)(OC2)C3=CC=CC=C3

Technology Process of Orthobenzoic acid, cyclic ester with 2-(hydroxymethyl)-2-methyl-1,3-propanediol

There total 5 articles about Orthobenzoic acid, cyclic ester with 2-(hydroxymethyl)-2-methyl-1,3-propanediol 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: 74.0%

(3-Methyloxetan-3-yl)methyl benzoate (173729-57-2) → 1-phenyl-4-methyl-2,6,7-trioxabicyclo<2.2.2>octane (70637-00-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 25 ℃; for 24h;

DOI:10.1016/S0040-4020(02)00701-9

Reference yield: 66.0%

2-(hydroxymethyl)-2-methylpropane-1,3-diol (77-85-0) + N,N-diethyl-α,α-difluorobenzylamine (90238-20-3) → 1-phenyl-4-methyl-2,6,7-trioxabicyclo<2.2.2>octane (70637-00-2)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 2h; Molecular sieve;

DOI:10.1055/s-0028-1083145

Reference yield:

2-(hydroxymethyl)-2-methylpropane-1,3-diol (77-85-0) + orthobenzoic acid trimethyl ester (707-07-3) → 1-phenyl-4-methyl-2,6,7-trioxabicyclo<2.2.2>octane (70637-00-2)

Guidance literature:

With toluene-4-sulfonic acid; at 100 ℃; under 0.1 Torr;

DOI:10.1021/jo00318a013

upstream raw materials:

2-(hydroxymethyl)-2-methylpropane-1,3-diol

orthobenzoic acid trimethyl ester

(3-Methyloxetan-3-yl)methyl benzoate

3-hydroxymethyl-3-methyloxethane

Downstream raw materials:

3-(methylthio)-6-phenyl-1,2,4,5-tetrazine

Refernces

• 1、 Tange, Seiko,Fukuhara, Tsuyoshi,Hara, Shoji. "Facile synthesis of bicyclo orthoesters and bicyclo amide acetals using α,α-difluoroalkylamines". experimental part. p. 3219 - 3222. Retrieved 2009/05/07.
• 2、 Rakus, Klaus,Verevkin, Sergey P.,Peng, Wei-Hong,Beckhaus, Hans-Dieter,Ruechardt, Christoph. "Geminal Substituent Effects, 11. The Anomeric Effect in Orthoesters - The Concept of Geminal Pairwise Interactions for the Interpretation of Standard Enthalpies of Formation". . p. 2059 - 2068. Retrieved 2007/10/03.