[5-(acetyloxymethyl)-6-bicyclo[2.2.1]hept-2-enyl]methyl acetate

Base Information

• Chemical Name: [5-(acetyloxymethyl)-6-bicyclo[2.2.1]hept-2-enyl]methyl acetate
• CAS No.: 6289-62-9
• Molecular Formula: C₁₃H₁₈O₄
• Molecular Weight: 238.284
• Mol file: 6289-62-9.mol

Synonyms:5-Norbornene-2,3-dimethanol,diacetate (6CI,8CI); Bicyclo[2.2.1]hept-5-ene-2,3-dimethanol, diacetate (9CI);NSC 5691

Chemical Property of [5-(acetyloxymethyl)-6-bicyclo[2.2.1]hept-2-enyl]methyl acetate

Chemical Property:

• Vapor Pressure: 0.00119mmHg at 25°C
• Boiling Point: 299.4°C at 760 mmHg
• Flash Point: 141.2°C
• PSA: 52.60000
• Density: 1.115g/cm³
• LogP: 1.55090

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [5-(acetyloxymethyl)-6-bicyclo[2.2.1]hept-2-enyl]methyl acetate

There total 7 articles about [5-(acetyloxymethyl)-6-bicyclo[2.2.1]hept-2-enyl]methyl acetate 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: 10.0%

acetic acid methyl ester (79-20-9) + (+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol (699-96-7,448922-61-0) → Acetic acid (1S,2R,3R,4R)-3-acetoxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (6289-62-9,62791-44-0,62841-50-3,123286-69-1,123286-71-5,133442-02-1,142507-56-0) + Acetic acid (1S,2R,3R,4R)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (123231-73-2,131320-81-5,131320-83-7,133399-12-9,133399-13-0,136459-08-0,136459-09-1,142507-55-9) + Acetic acid (1R,2R,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (123231-73-2,131320-81-5,131320-83-7,133399-12-9,133399-13-0,136459-08-0,136459-09-1,142507-55-9)

Guidance literature:

for 44h; Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4020(01)80984-4

Reference yield:

acetic acid methyl ester (79-20-9) + (-)-2-endo-3-exo-Bis(hydroxymethyl)-bicyclo<2.2.1>hept-5-ene (79516-58-8,448922-61-0) → Acetic acid (1S,2R,3R,4R)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (123231-73-2,131320-81-5,131320-83-7,133399-12-9,133399-13-0,136459-08-0,136459-09-1,142507-55-9) + Acetic acid (1R,2R,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (123231-73-2) + Acetic acid (1S,2R,3R,4R)-3-acetoxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (6289-62-9,62791-44-0,62841-50-3,123286-69-1,123286-71-5,133442-02-1,142507-56-0)

Guidance literature:

porcine pancreatic lipase; for 44h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4039(00)97284-8

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → Acetic acid (1S,2R,3R,4R)-3-acetoxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (6289-62-9,62791-44-0,62841-50-3,123286-69-1,123286-71-5,133442-02-1,142507-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / toluene / Heating

2: LAH

With lithium aluminium tetrahydride; In toluene;

DOI:10.1016/S0960-894X(98)00143-7

upstream raw materials:

acetic acid methyl ester

(-)-2-endo-3-exo-Bis(hydroxymethyl)-bicyclo<2.2.1>hept-5-ene

(+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol

acetyl chloride

Downstream raw materials:

(-)-2-endo-3-exo-Bis(hydroxymethyl)-bicyclo<2.2.1>hept-5-ene

(+)-2-endo-3-exo-Bis(hydroxymethyl)-bicyclo<2.2.1>hept-5-ene