3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester

Base Information

• Chemical Name: 3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester
• CAS No.: 67045-68-5
• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.392
• Mol file: 67045-68-5.mol

Synonyms:3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester

Chemical Property of 3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester

There total 15 articles about 3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl 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: 80.0%

3-methyl-6-(3(R)-methyl-4,5-dihydroxypentyl)salicylic acid benzyl ester (75371-90-3,84911-53-5,84912-01-6,87598-86-5,87599-04-0) → 3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester (67045-68-5)

Guidance literature:

With sodium periodate; In methanol; water; for 2h; Ambient temperature;

DOI:10.1021/ja00345a055

Reference yield:

2-(dibenzylamino)-3-methyl-6-(3(R)-methyl-4-pentenyl)benzoic acid methyl ester (75371-80-1) → 3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester (67045-68-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / 4-methylmorpholine 4-oxide, OsO₄ / H₂O; 2-methyl-propan-2-ol / 24 h / Ambient temperature

2: 93 percent / H₂ / Pd/C / ethanol / 10 h / 2585.7 Torr

3: 85 percent / HBF₄, isoamyl nitrite / ethanol / 0.5 h / 0 °C

4: 98 percent / p-toluenesulfonic acid / acetone / 0.25 h / Ambient temperature

5: KH / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) 0 deg C, 1 h, 3.) room temperature, 0.5 h

6: 1.) BuLi, n-propanethiol / 1.) pentane, hexane, 0 deg C, 15 min, 2.) HMPA, 0 deg C, 10 min, room temperature, 45 min, 3.) room temperature, 2 h

7: 10percent HCl / H₂O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h

8: 80 percent / NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; tetrafluoroboric acid; n-butyllithium; 1-thiopropane; hydrogen; potassium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; isopentyl nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; acetone; tert-butyl alcohol;

DOI:10.1021/ja00345a055

Reference yield:

2-(dibenzylamino)-3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)benzoic acid methyl ester (75371-86-7,84911-47-7,84911-95-5) → 3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester (67045-68-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / H₂ / Pd/C / ethanol / 10 h / 2585.7 Torr

2: 85 percent / HBF₄, isoamyl nitrite / ethanol / 0.5 h / 0 °C

3: 98 percent / p-toluenesulfonic acid / acetone / 0.25 h / Ambient temperature

4: KH / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) 0 deg C, 1 h, 3.) room temperature, 0.5 h

5: 1.) BuLi, n-propanethiol / 1.) pentane, hexane, 0 deg C, 15 min, 2.) HMPA, 0 deg C, 10 min, room temperature, 45 min, 3.) room temperature, 2 h

6: 10percent HCl / H₂O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h

7: 80 percent / NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

With hydrogenchloride; sodium periodate; tetrafluoroboric acid; n-butyllithium; 1-thiopropane; hydrogen; potassium hydride; toluene-4-sulfonic acid; isopentyl nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; acetone;

DOI:10.1021/ja00345a055

upstream raw materials:

3-methyl-6-(3(R)-methyl-4,5-dihydroxypentyl)salicylic acid benzyl ester

3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid methyl ester

2-(dibenzylamino)-3-methyl-6-(3(R)-methyl-4-pentenyl)benzoic acid methyl ester

3-methyl-6-(3(R)-methyl-4,5-dihydroxypentyl)salicylic acid methyl ester

Downstream raw materials:

lasalocid benzyl ester

Benzyl 23-O-benzyloxymethylisolasalocid A

2-Acetoxy-3-methyl-6-((R)-3-methyl-4-oxo-butyl)-benzoic acid benzyl ester

lasalocid (X 537 A)