Benzyl 3-hydroxytetradecanoate

Base Information

• Chemical Name: Benzyl 3-hydroxytetradecanoate
• CAS No.: 88862-84-4
• Molecular Formula: C21H34O3
• Molecular Weight: 334.49300
• DSSTox Substance ID: DTXSID80441235
• Mol file: 88862-84-4.mol

Synonyms:Benzyl 3-hydroxytetradecanoate;88862-84-4;benzyl 3-hydroxymyristate;SCHEMBL6370572;DTXSID80441235;NRNRXBHTCKDUNQ-UHFFFAOYSA-N

Chemical Property of Benzyl 3-hydroxytetradecanoate

Chemical Property:

• PSA: 46.53000
• LogP: 5.40170
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 334.25079494
• Heavy Atom Count: 24
• Complexity: 298

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(CC(=O)OCC1=CC=CC=C1)O

Technology Process of Benzyl 3-hydroxytetradecanoate

There total 5 articles about Benzyl 3-hydroxytetradecanoate 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: 97.0%

(R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9) + benzyl chloride (100-44-7) → 3-hydroxy-D-tetradecanoic acid benzyl ester (88862-84-4)

Guidance literature:

In tetrahydrofuran; dimethyl sulfoxide; at 50 ℃;

Reference yield: 61.0%

(R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9) + benzyl bromide (100-39-0) → 3-hydroxy-D-tetradecanoic acid benzyl ester (88862-84-4)

Guidance literature:

With triethylamine; In ethyl acetate; for 72h; Ambient temperature;

DOI:10.1248/cpb.39.1994

Reference yield:

methyl (R)-3-hydroxytetradecanoate (76062-97-0) → 3-hydroxy-D-tetradecanoic acid benzyl ester (88862-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / ethanol

2: Et₃N; tetrabutylammonium iodide / ethyl acetate / 18 h / 20 °C

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; triethylamine; In ethanol; ethyl acetate;

DOI:10.1021/jm060482a

upstream raw materials:

(R)-3-hydroxytetradecanoic acid

benzyl bromide

benzyl chloride

4-undecyloxetan-2-one

Downstream raw materials:

benzyl (R)-3-dodecanoyloxytetradecanoate

1-O-acetyl-2-deoxy-4-O-diphenylphosphono-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-<(R)-3-(2,2,2-trichloroethoxycarbonyloxy)tetradecanoyl>-D-glucopyranose

allyl 2-deoxy-4-O-diphenylphosphono-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-<(R)-3-(2,2,2-trichloroethoxycarbonyloxy)tetradecanoyl>-α-D-glucopyranoside

(R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester

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