1-phenylbut-3-ene-1,2-diol

Base Information

• Chemical Name: 1-phenylbut-3-ene-1,2-diol
• CAS No.: 19261-14-4
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.204
• Mol file: 19261-14-4.mol

Synonyms:1-phenylbut-3-ene-1,2-diol

Chemical Property of 1-phenylbut-3-ene-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-phenylbut-3-ene-1,2-diol

There total 26 articles about 1-phenylbut-3-ene-1,2-diol 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%

benzaldehyde (100-52-7) + acetic acid 3-bromo-1-propenyl ester (4957-34-0) → 1-phenylbut-3-ene-1,2-diol (19261-14-4)

Guidance literature:

acetic acid 3-bromo-1-propenyl ester; With indium; In tetrahydrofuran; at 0 - 25 ℃; for 4h;

benzaldehyde; In tetrahydrofuran; at -78 ℃; for 4h;

With potassium carbonate; In methanol; water; at 25 ℃; Further stages.;

DOI:10.1021/jo0262457

Reference yield: 77.0%

benzaldehyde (100-52-7) + (E)-3-bromoprop-1-enyl benzoate (500756-90-1) → 1-phenylbut-3-ene-1,2-diol (19261-14-4)

Guidance literature:

(E)-3-bromoprop-1-enyl benzoate; With indium; In tetrahydrofuran; at 0 - 25 ℃; for 4h;

benzaldehyde; In tetrahydrofuran; at 0 ℃; for 4h;

With potassium carbonate; In methanol; water; at 25 ℃; Further stages.;

DOI:10.1021/jo0262457

Reference yield: 13.0%

benzaldehyde (100-52-7) + acetic acid 3-bromo-1-propenyl ester (4957-34-0) → 1-phenylbut-3-ene-1,2-diol (19261-14-4) + 4-phenyl-4-acetoxybut-1-en-3-ol + 3,4-diacetoxy-4-phenylbut-1-ene + 3,4-diacetoxy-4-phenylbut-1-ene

Guidance literature:

acetic acid 3-bromo-1-propenyl ester; With indium; In tetrahydrofuran; at 0 - 25 ℃; for 4h;

benzaldehyde; In tetrahydrofuran; at 0 ℃; for 4h; Further byproducts given;

DOI:10.1021/jo0262457

upstream raw materials:

benzaldehyde

acrolein

acetic acid 3-bromo-1-propenyl ester

(E)-3-bromoprop-1-enyl benzoate

Downstream raw materials:

4-hydroxy-4-phenyl-1-butene-3-one

4,5-trans-2,2-dimethyl-4-phenyl-5-ethenyl-1,3-dioxolane

4,5-cis-2,2-dimethyl-4-phenyl-5-ethenyl-1,3-dioxolane

1-phenylbut-3-en-2-one

Refernces

• 1、 Kister, Jeremy,Nuhant, Philippe,Lira, Ricardo,Sorg, Achim,Roush, William R.. "Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin". supporting information; experimental part. p. 1868 - 1871. Retrieved 2011/06/22.
• 2、 Bottoni,Lombardo,Miscione,Pujol Algue,Trombini. "3-bromozinc propenyl esters: An experimental and theoretical study of the unique stereocrossover observed in their addition to aromatic and aliphatic aldehydes". . p. 418 - 426. Retrieved 2008/09/17.