8-(4-benzoylbenzoyloxy)-geraniol

Base Information

• Chemical Name: 8-(4-benzoylbenzoyloxy)-geraniol
• CAS No.: 183376-17-2
• Molecular Formula: C₂₄H₂₆O₄
• Molecular Weight: 378.468
• Mol file: 183376-17-2.mol

Synonyms:8-(4-benzoylbenzoyloxy)-geraniol

Chemical Property of 8-(4-benzoylbenzoyloxy)-geraniol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-(4-benzoylbenzoyloxy)-geraniol

There total 7 articles about 8-(4-benzoylbenzoyloxy)-geraniol 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: 97.0%

4-Benzoyl-benzoic acid (2E,6E)-8-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienyl ester (618405-54-2) → 8-(4-benzoylbenzoyloxy)-geraniol (183376-17-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/ja036178d

Reference yield: 42.0%

4-Benzoyl-benzoic acid (2E,6E)-8-(2-chloro-acetoxy)-2,6-dimethyl-octa-2,6-dienyl ester (183376-16-1) → 8-(4-benzoylbenzoyloxy)-geraniol (183376-17-2)

Guidance literature:

With ammonium hydroxide; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo9602736

Reference yield:

Geraniol (106-24-1) → 8-(4-benzoylbenzoyloxy)-geraniol (183376-17-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

2.1: SeO₂; t-BuOOH; salycylic acid / CH₂Cl₂; H₂O; various solvent(s) / 12 h

2.2: 50 percent / NaBH₄ / methanol

3.1: 58 percent / DMAP; diisopropylcarbodiimide / CH₂Cl₂ / 20 °C

4.1: 97 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

With tert.-butylhydroperoxide; dmap; selenium(IV) oxide; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; salicylic acid; diisopropyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; 3.1: Steglich reaction;

DOI:10.1021/ja036178d

upstream raw materials:

4-Benzoyl-benzoic acid (2E,6E)-8-(2-chloro-acetoxy)-2,6-dimethyl-octa-2,6-dienyl ester

4-Benzoyl-benzoic acid (2E,6E)-8-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienyl ester

Geraniol

geraniol tert-butyldimethylsilyl ether

Downstream raw materials:

4-Benzoyl-benzoic acid (2E,6E)-8-chloro-2,6-dimethyl-octa-2,6-dienyl ester

Refernces

• 1、 Gaon, Igor,Turek, Tammy C.,Weller, Valerie A.,Edelstein, Rebecca L.,Singh, Satinder K.,Distefano, Mark D.. "Photoactive analogs of farnesyl pyrophosphate containing benzoylbenzoate esters: Synthesis and application to photoaffinity labeling of yeast protein farnesyltransferase". . p. 7738 - 7745. Retrieved 2007/10/03.