(R)-2-(4-Methoxybenzyl)-1,3-propanediol 1-acetate

Base Information

• Chemical Name: (R)-2-(4-Methoxybenzyl)-1,3-propanediol 1-acetate
• CAS No.: 174417-66-4
• Molecular Formula: C₁₃H₁₈O₄
• Molecular Weight: 238.284
• DSSTox Substance ID: DTXSID001170903
• Nikkaji Number: J699.083E
• Mol file: 174417-66-4.mol

Synonyms:DTXSID001170903;(R)-2-(4-Methoxybenzyl)-1,3-propanediol 1-acetate;1,3-Propanediol, 2-[(4-methoxyphenyl)methyl]-, monoacetate, (R)-;174417-66-4

Chemical Property of (R)-2-(4-Methoxybenzyl)-1,3-propanediol 1-acetate

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 238.12050905
• Heavy Atom Count: 17
• Complexity: 222

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC(CC1=CC=C(C=C1)OC)CO
• Isomeric SMILES: CC(=O)OC[C@H](CC1=CC=C(C=C1)OC)CO

Technology Process of (R)-2-(4-Methoxybenzyl)-1,3-propanediol 1-acetate

There total 3 articles about (R)-2-(4-Methoxybenzyl)-1,3-propanediol 1-acetate 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: 96.0%

vinyl acetate (108-05-4,9003-20-7) + 2-(p-methoxybenzyl)propane-1,3-diol (63559-26-2) → (R)-3-hydroxy-2-(p-methoxybenzyl)propyl acetate (174417-66-4)

Guidance literature:

With Lipase PS; 2,6-di-tert-butyl-4-methyl-phenol; In di-isopropyl ether; water; for 1.5h; Ambient temperature;

DOI:10.3987/COM-95-7232

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (R)-3-hydroxy-2-(p-methoxybenzyl)propyl acetate (174417-66-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / 1.) sodium hydride / 1.) mineral oil, THF, r.t., 30 min; 2.) THF, 4 h, reflux

2: 95 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

3: 96 percent / 2,6-di-tert-butyl-p-cresole, Lipase PS / diisopropyl ether; H₂O / 1.5 h / Ambient temperature

With lithium aluminium tetrahydride; Lipase PS; 2,6-di-tert-butyl-4-methyl-phenol; sodium hydride; In tetrahydrofuran; di-isopropyl ether; water;

DOI:10.3987/COM-95-7232

Reference yield:

2-(4-methoxybenzyl)malonic acid diethyl ester (6335-37-1) → (R)-3-hydroxy-2-(p-methoxybenzyl)propyl acetate (174417-66-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

2: 96 percent / 2,6-di-tert-butyl-p-cresole, Lipase PS / diisopropyl ether; H₂O / 1.5 h / Ambient temperature

With lithium aluminium tetrahydride; Lipase PS; 2,6-di-tert-butyl-4-methyl-phenol; In tetrahydrofuran; di-isopropyl ether; water;

DOI:10.3987/COM-95-7232

upstream raw materials:

vinyl acetate

2-(p-methoxybenzyl)propane-1,3-diol

p-methoxybenzyl chloride

2-(4-methoxybenzyl)malonic acid diethyl ester

Downstream raw materials:

(R)-3-(2-tetrahydropyranyloxy)-2-(p-methoxybenzyl)propyl acetate

(S)-3-acetoxy-2-(p-methoxybenzyl)propyl pivaloate

(S)-3-(tert-butyldimethylsilyloxy)-2-(p-methoxybenzyl)propyl acetate

Acetic acid (S)-2-methanesulfonyloxymethyl-3-(4-methoxy-phenyl)-propyl ester