α-(o-tolyl)-γ-butyrolactone

Base Information

• Chemical Name: α-(o-tolyl)-γ-butyrolactone
• CAS No.: 1291082-19-3
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.215
• Mol file: 1291082-19-3.mol

Synonyms:α-(o-tolyl)-γ-butyrolactone

Chemical Property of α-(o-tolyl)-γ-butyrolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of α-(o-tolyl)-γ-butyrolactone

There total 5 articles about α-(o-tolyl)-γ-butyrolactone 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: 93.0%

carbon monoxide (201230-82-2) + (E)-3-(2-methylphenyl)-2-propenol (501922-06-1) → α-(o-tolyl)-γ-butyrolactone (1291082-19-3) + 3-hydroxy-2-(2-methylbenzyl)propanoic acid (1291082-09-1)

Guidance literature:

(E)-3-(2-methylphenyl)-2-propenol; With dicarbonylacetylacetonato rhodium (I); C₁₇H₂₀NOP; toluene-4-sulfonic acid; In benzene; at 45 ℃; for 0.166667h; Inert atmosphere;

carbon monoxide; With hydrogen; In benzene; at 45 ℃; for 16h; under 2585.81 Torr;

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; for 6h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol200782d

Reference yield: 41.0%

4-(benzyloxy)-1-(pyrrolidin-1-yl)butan-1-one (1301601-31-9) → α-(o-tolyl)-γ-butyrolactone (1291082-19-3)

Guidance literature:

With 2,4,6-trimethyl-pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 20 - 120 ℃; for 0.583333h; Inert atmosphere; Microwave irradiation;

DOI:10.1002/chem.201003591

Reference yield:

methyl (E)-3-(2-methylphenyl)-2-propenoate (70625-62-6,75950-75-3,130451-86-4) → α-(o-tolyl)-γ-butyrolactone (1291082-19-3) + 3-hydroxy-2-(2-methylbenzyl)propanoic acid (1291082-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 0.5 h / Inert atmosphere

2.1: dicarbonylacetylacetonato rhodium (I); C₁₇H₂₀NOP; toluene-4-sulfonic acid / benzene / 0.17 h / 45 °C / Inert atmosphere

2.2: 16 h / 45 °C / 2585.81 Torr

2.3: 6 h / Inert atmosphere

With aluminum (III) chloride; lithium aluminium tetrahydride; dicarbonylacetylacetonato rhodium (I); C₁₇H₂₀NOP; toluene-4-sulfonic acid; In diethyl ether; benzene; 2.3: Pinnick oxidation;

DOI:10.1021/ol200782d

upstream raw materials:

4-(benzyloxy)-1-(pyrrolidin-1-yl)butan-1-one

carbon monoxide

(E)-3-(2-methylphenyl)-2-propenol

methyl (E)-3-(2-methylphenyl)-2-propenoate