(2R,3R,5E)-2-hydroxy-3-methyl-5-heptenyl benzoate

Base Information

• Chemical Name: (2R,3R,5E)-2-hydroxy-3-methyl-5-heptenyl benzoate
• CAS No.: 81135-50-4
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 81135-50-4.mol

Synonyms:(2R,3R,5E)-2-hydroxy-3-methyl-5-heptenyl benzoate

Chemical Property of (2R,3R,5E)-2-hydroxy-3-methyl-5-heptenyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,5E)-2-hydroxy-3-methyl-5-heptenyl benzoate

There total 8 articles about (2R,3R,5E)-2-hydroxy-3-methyl-5-heptenyl benzoate 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: 90.0%

(2R,3R,5E)-3-methyl-5-heptene-1,2-diol (84906-49-0) + benzoyl chloride (98-88-4) → (2R,3R,5E)-2-hydroxy-3-methyl-5-heptenyl benzoate (81135-50-4)

Guidance literature:

With pyridine; In tetrahydrofuran; for 0.666667h; Ambient temperature;

DOI:10.1002/hlca.19830660742

Reference yield:

(2R,3R)-1,4-bis(benzyloxy)-3-methyl-2-butanol (84906-48-9) → (2R,3R,5E)-2-hydroxy-3-methyl-5-heptenyl benzoate (81135-50-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / H₂ / 10percent Pd/C / aq. ethanol / 2 h

2: 85 percent / 1) TsOH*H₂O, 2) TsOH*H₂O / 1) benzene, reflux, 2 h, 2) acetone, reflux 16 h

3: 91 percent / pyridine / CHCl₃ / 1) 45 min; 2) 35 deg C, 3 h

4: 90 percent / dimethylsulfoxide / 72 h / Ambient temperature

5: 82 percent / 20percent DIBAH / hexane / 1.5 h / -78 °C

6: 15percent BuLi/hexane / tetrahydrofuran; diethyl ether / Ambient temperature

7: 94 percent / 1 N aq. HCl / tetrahydrofuran / 48 h / Ambient temperature

8: 90 percent / pyridine / tetrahydrofuran / 0.67 h / Ambient temperature

With pyridine; hydrogenchloride; n-butyllithium; hexane; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; chloroform; dimethyl sulfoxide;

DOI:10.1002/hlca.19830660742

Reference yield:

*R*)>-α,2,2-trimethyl-1,3-dioxolane-4-ethanol (74243-89-3) → (2R,3R,5E)-2-hydroxy-3-methyl-5-heptenyl benzoate (81135-50-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / pyridine / CHCl₃ / 1) 45 min; 2) 35 deg C, 3 h

2: 90 percent / dimethylsulfoxide / 72 h / Ambient temperature

3: 82 percent / 20percent DIBAH / hexane / 1.5 h / -78 °C

4: 15percent BuLi/hexane / tetrahydrofuran; diethyl ether / Ambient temperature

5: 94 percent / 1 N aq. HCl / tetrahydrofuran / 48 h / Ambient temperature

6: 90 percent / pyridine / tetrahydrofuran / 0.67 h / Ambient temperature

With pyridine; hydrogenchloride; n-butyllithium; hexane; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; chloroform; dimethyl sulfoxide;

DOI:10.1002/hlca.19830660742

upstream raw materials:

(2R,3R,5E)-3-methyl-5-heptene-1,2-diol

benzoyl chloride

*R^*)>-α,2,2-trimethyl-1,3-dioxolane-4-ethanol

(2R,3R)-3-methyl-butan-1,2,4-triol