(+/-)-(1R,2S,3R,4S)-3-hydroxybicyclo[2.2.1]heptan-2-yl benzoate

Base Information

• Chemical Name: (+/-)-(1R,2S,3R,4S)-3-hydroxybicyclo[2.2.1]heptan-2-yl benzoate
• CAS No.: 77085-41-7
• Molecular Formula: C₁₄H₁₆O₃
• Molecular Weight: 232.279
• Mol file: 77085-41-7.mol

Synonyms:(+/-)-(1R,2S,3R,4S)-3-hydroxybicyclo[2.2.1]heptan-2-yl benzoate

Chemical Property of (+/-)-(1R,2S,3R,4S)-3-hydroxybicyclo[2.2.1]heptan-2-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(1R,2S,3R,4S)-3-hydroxybicyclo[2.2.1]heptan-2-yl benzoate

There total 15 articles about (+/-)-(1R,2S,3R,4S)-3-hydroxybicyclo[2.2.1]heptan-2-yl 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: 91.0%

(1R,2S,3R,4S)-bicyclo[2.2.1]heptane-2,3-diol (16329-23-0) + benzoyl chloride (98-88-4) → (+/-)-(1R,2S,3R,4S)-3-hydroxybicyclo[2.2.1]heptan-2-yl benzoate (77085-41-7)

Guidance literature:

In dichloromethane; at 0 ℃; Inert atmosphere;

DOI:10.1039/c1cc11654a

Reference yield: 90.7%

dioxa-3,5 endo phenyl-4 anti tricyclo<5.2.1.02,6>decane (31112-51-3,31112-52-4,77341-47-0,77341-48-1) → benzoyloxy-2 endo hydroxy-3 endo bicyclo <2.2.1> heptane (77085-41-7,77299-90-2) + bromo-2 exo hydroxy-3 endo bicyclo<2.2.1>heptane (77085-37-1,77341-49-2)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; for 3h; Heating;

DOI:10.1016/0040-4020(80)80151-7

Reference yield: 29.5%

dioxa-3,5 exo phenyl-4 syn tricyclo<5.2.1.02,6>decane (31112-52-4) → Benzoic acid (1S,2R,4S)-2-bromo-bicyclo[2.2.1]hept-7-yl ester (77085-38-2,77085-39-3,77085-40-6) + Benzoic acid (1S,2S,4S,7R)-2-bromo-bicyclo[2.2.1]hept-7-yl ester + Benzoic acid (1R,2R,4R,7R)-2-bromo-bicyclo[2.2.1]hept-7-yl ester + (+/-)-(1R,2S,3R,4S)-3-hydroxybicyclo[2.2.1]heptan-2-yl benzoate (77085-41-7) + bromo-2 endo benzoyloxy-3 exo bicyclo<2.2.1>heptane (77085-37-1,77341-49-2)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; for 3h; Product distribution; Heating; variation of time and quantity of NBS;

DOI:10.1016/0040-4020(80)80152-9

upstream raw materials:

(1R,2S,3R,4S)-bicyclo[2.2.1]heptane-2,3-diol

(2,2,2-trimethoxyethyl)benzene

trityl tetrafluoroborate

dioxa-3,5 exo phenyl-4 syn tricyclo<5.2.1.0^2,6>decane

Downstream raw materials:

bromo-2 exo benzoyloxy-7 syn bicyclo<2.2.1>heptane

bromo-2 endo benzoyloxy-3 exo bicyclo<2.2.1>heptane

(1S,2R,3R,4R,5R,6S)-6-Benzoyloxy-3-chloromethyl-5-hydroxy-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

(1S,2R,3R,4R,5R,6S)-5-Benzoyloxy-3-chloromethyl-6-hydroxy-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester