ChemInform Abstract: Synthesis of (Z)‐11‐Hexadecen‐1‐yl Acetate and Its (E)‐Isomer

Vig, O. P.; Sharma, M. L.; Vohra, N.; Sabharwal, A.; Huq, M. A.

doi:10.1002/chin.198817357

Cited by 1 publication

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Bromoalkanols and bromocarboxylic acids are important intermediates in the synthesis of insect pheromones and other naturally occurring products, as they provide two reactive sites for further reaction. After suitable protection of alcoholic/acidic groups, these compounds can be important precursors for the formation of C−C bonds − and conversion to Wittig or to a Grignard reagent …”

Section: Discussionmentioning

confidence: 99%

Functional Group Transformations of Diols, Cyclic Ethers, and Lactones Using Aqueous Hydrobromic Acid and Phase Transfer Catalyst under Microwave Irradiation

Kad

Kaur

Bhandari

et al. 2003

Org. Process Res. Dev.

View full text Add to dashboard Cite

Synthesis of bromoalkanols has been achieved from diols, ethers, and lactones using aq HBr (48%) and tetrabutylammonium iodide/bromide as phase transfer catalyst under microwave irradiation. This environmentally benign route provides enhanced yields of products and does away with the use of benzene as compared to existing conventional methods. DiscussionBromoalkanols and bromocarboxylic acids are important intermediates in the synthesis of insect pheromones and other naturally occurring products, as they provide two reactive sites for further reaction. After suitable protection of alcoholic/acidic groups, these compounds can be important precursors for the formation of C-C bonds 1-3 and conversion to Wittig 4 or to a Grignard reagent. 5 Various methods have been reported in the literature to achieve this goal; however, they require reaction of diols with aqueous hydrogen bromide using a continuous extraction apparatus employing nonpolar solvents such as cyclohexane 5 (72 h) or toluene 6 (16 h). Kang et al. 7 have prepared bromoalkanols by refluxing a mixture of diols with 48% aq HBr in benzene in 40-90% yield; dibromide (13%) and unreacted diol (2%) were also present. Now, microwave energy has been used in a wide variety of reactions, 8-12 owing to their high heating efficiencies with remarkable rate enhancement and dramatic reduction in

show abstract

Section: Discussionmentioning

confidence: 99%

Functional Group Transformations of Diols, Cyclic Ethers, and Lactones Using Aqueous Hydrobromic Acid and Phase Transfer Catalyst under Microwave Irradiation

Kad

Kaur

Bhandari

et al. 2003

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Synthesis of (Z)‐11‐Hexadecen‐1‐yl Acetate and Its (E)‐Isomer

Abstract: 357ChemInform Abstract ((Va), a sex pheromone of Sesamia inferenes, and (Vb), a sex pheromone of Brachmia macroscopa).

Cited by 1 publication

References 0 publications

Functional Group Transformations of Diols, Cyclic Ethers, and Lactones Using Aqueous Hydrobromic Acid and Phase Transfer Catalyst under Microwave Irradiation

Functional Group Transformations of Diols, Cyclic Ethers, and Lactones Using Aqueous Hydrobromic Acid and Phase Transfer Catalyst under Microwave Irradiation

Contact Info

Product

Resources

About