2,3-Butadienoic acid, 2-(hydroxymethyl)-, phenylmethyl ester

Base Information

• Chemical Name: 2,3-Butadienoic acid, 2-(hydroxymethyl)-, phenylmethyl ester
• CAS No.: 877167-87-8
• Molecular Formula: C12H12O3
• Molecular Weight: 204.225
• Mol file: 877167-87-8.mol

Synonyms:

Chemical Property of 2,3-Butadienoic acid, 2-(hydroxymethyl)-, phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-Butadienoic acid, 2-(hydroxymethyl)-, phenylmethyl ester

There total 2 articles about 2,3-Butadienoic acid, 2-(hydroxymethyl)-, phenylmethyl ester 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: 60.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + buta-2,3-dienoic acid benzyl ester (187661-86-5) → benzyl 2-(hydroxymethyl)buta-2,3-dienoate (877167-87-8)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In tetrahydrofuran; at -10 - 18 ℃;

DOI:10.1002/ejoc.200500609

Reference yield:

(carbobenzyloxymethylene)triphenylphosphorane (15097-38-8) → benzyl 2-(hydroxymethyl)buta-2,3-dienoate (877167-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

1.2: 82 percent / CH₂Cl₂ / 0.83 h

2.1: 60 percent / DABCO / tetrahydrofuran / -10 - 18 °C

With 1,4-diaza-bicyclo[2.2.2]octane; triethylamine; In tetrahydrofuran; dichloromethane; 2.1: Baylis-Hillman reaction;

DOI:10.1002/ejoc.200500609

Reference yield: 79.0%

benzyl 2-(hydroxymethyl)buta-2,3-dienoate (877167-87-8) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → benzyl 2-(triisopropylsilanyloxymethyl)buta-2,3-dienoate (877167-88-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/ejoc.200500609

upstream raw materials:

formaldehyd

buta-2,3-dienoic acid benzyl ester

(carbobenzyloxymethylene)triphenylphosphorane

Downstream raw materials:

benzyl 2-(benzyloxymethyl)buta-2,3-dienoate

benzyl 2-(triisopropylsilanyloxymethyl)buta-2,3-dienoate

{[2-(bromomethyl)buta-2,3-dien-1-yl]oxymethyl}benzene

2-((benzyloxy)methyl)buta-2,3-dien-1-ol