15-Methyloxacyclopentadecan-2-one

Base Information

• Chemical Name: 15-Methyloxacyclopentadecan-2-one
• CAS No.: 32539-85-8
• Molecular Formula: C15H28O2
• Molecular Weight: 240.38
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID90865640
• Nikkaji Number: J133.799H
• Wikidata: Q106654097
• Mol file: 32539-85-8.mol

Synonyms:15-Methyloxacyclopentadecan-2-one;32539-85-8;15-methyl-1-oxacyclopentadecan-2-one;15-methyl-oxacyclopentadecan-2-one;Oxacyclopentadecan-2-one, 15-methyl-;14-pentadecanolide;SCHEMBL3075568;DTXSID90865640;LVECZGHBXXYWBO-UHFFFAOYSA-N

Chemical Property of 15-Methyloxacyclopentadecan-2-one

Chemical Property:

• Vapor Pressure: 8.87E-05mmHg at 25°C
• Melting Point: 34-38 °C(lit.)
• Boiling Point: 137 °C2 mm Hg(lit.)
• Flash Point: 141.1°C
• PSA: 26.30000
• Density: 0.878g/cm³
• LogP: 4.61290
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 240.208930132
• Heavy Atom Count: 17
• Complexity: 201

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCCCCCCCCCCC(=O)O1

Technology Process of 15-Methyloxacyclopentadecan-2-one

There total 9 articles about 15-Methyloxacyclopentadecan-2-one 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:

12-bromododecanol (3344-77-2) → (+/-)-14-hydroxypentadecanoic acid lactone (32539-85-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / pyridinium chlorochromate / Celite / CH₂Cl₂ / 1.5 h

2: 87 percent / diethyl ether / 16 h / Ambient temperature

3: 1.) p-toluene-sulfonic acid, 2.) NaI / 1.) THF, RT, 1 h, 2.) RT, 24 h, acetone

4: 39 percent / n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 degC, 30 min and RT, 4 h

5: 1.) O₂, 2.) p-toluenesulfonic acid / 1.) Sensitox / 1.) CH₂Cl₂, 30 min, irradiation, 2.) benzene, 24 h, reflux

With n-butyllithium; oxygen; toluene-4-sulfonic acid; diisopropylamine; pyridinium chlorochromate; sodium iodide; Celite; Sensitox; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4020(01)93281-8

Reference yield:

12-bromododecanoic acid (73367-80-3) → (+/-)-14-hydroxypentadecanoic acid lactone (32539-85-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / borane, HCl / tetrahydrofuran; methanol / 2 h

2: 82 percent / pyridinium chlorochromate / Celite / CH₂Cl₂ / 1.5 h

3: 87 percent / diethyl ether / 16 h / Ambient temperature

4: 1.) p-toluene-sulfonic acid, 2.) NaI / 1.) THF, RT, 1 h, 2.) RT, 24 h, acetone

5: 39 percent / n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 degC, 30 min and RT, 4 h

6: 1.) O₂, 2.) p-toluenesulfonic acid / 1.) Sensitox / 1.) CH₂Cl₂, 30 min, irradiation, 2.) benzene, 24 h, reflux

With hydrogenchloride; n-butyllithium; borane; oxygen; toluene-4-sulfonic acid; diisopropylamine; pyridinium chlorochromate; sodium iodide; Celite; Sensitox; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4020(01)93281-8

Reference yield:

13-bromo-2-hydroxytridecane (81819-08-1) → (+/-)-14-hydroxypentadecanoic acid lactone (32539-85-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) p-toluene-sulfonic acid, 2.) NaI / 1.) THF, RT, 1 h, 2.) RT, 24 h, acetone

2: 39 percent / n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 degC, 30 min and RT, 4 h

3: 1.) O₂, 2.) p-toluenesulfonic acid / 1.) Sensitox / 1.) CH₂Cl₂, 30 min, irradiation, 2.) benzene, 24 h, reflux

With n-butyllithium; oxygen; toluene-4-sulfonic acid; diisopropylamine; sodium iodide; Sensitox; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(01)93281-8

upstream raw materials:

2-(13-hydroxytetradecanyl)-4,5-diphenyloxazole

14-hydroxypentadecanoic acid

benzenesulfonic acid

benzene

Refernces

• 1、 Wasserman, Harry H.,Gambale, Ronald J.,Pulwer, Mitchell J.. "ACTIVATED CARBOXYLATES FROM THE PHOTOOXYGENATION OF OXAZOLES; APPLICATION TO THE SYNTHESIS OF RECIFEIOLIDE, CURVULARIN AND MACROLIDES". . p. 4059 - 4067. Retrieved 2007/10/02.