DL-(1,5/4)-4,7-O-benzylidene-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol

Base Information

• Chemical Name: DL-(1,5/4)-4,7-O-benzylidene-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol
• CAS No.: 142573-32-8
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 142573-32-8.mol

Synonyms:DL-(1,5/4)-4,7-O-benzylidene-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol

Chemical Property of DL-(1,5/4)-4,7-O-benzylidene-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of DL-(1,5/4)-4,7-O-benzylidene-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol

There total 5 articles about DL-(1,5/4)-4,7-O-benzylidene-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol 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:

benzaldehyde dimethyl acetal (1125-88-8) → DL-(1,5/4)-4,7-O-benzylidene-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol (142573-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / acetonitrile / 0.25 h

2: 1.) NaH / 1.) N,N-DMF, 0 deg C, 30 min, 2.) 1 h

With sodium hydride; toluene-4-sulfonic acid; In acetonitrile;

Reference yield:

(1R,2S,4R)-2-Hydroxymethyl-cyclohexane-1,4-diol (142573-30-6) → DL-(1,5/4)-4,7-O-benzylidene-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol (142573-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / acetonitrile / 0.25 h

2: 1.) NaH / 1.) N,N-DMF, 0 deg C, 30 min, 2.) 1 h

With sodium hydride; toluene-4-sulfonic acid; In acetonitrile;

Reference yield:

(+/-)-endo-7-oxabicyclo<2.2.1>-heptane-2-carboxylic acid (19800-01-2,38263-55-7,38263-56-8,64589-27-1) → DL-(1,5/4)-4,7-O-benzylidene-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol (142573-32-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 35 percent / 85percent HOAc, H₂SO₄ / 20 h / 80 °C

2: BH₃ / tetrahydrofuran / 48 h / Ambient temperature

3: p-toluenesulfonic acid / acetonitrile / 0.25 h

4: 1.) NaH / 1.) N,N-DMF, 0 deg C, 30 min, 2.) 1 h

With sulfuric acid; borane; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; acetonitrile;

upstream raw materials:

DL-(1,5/4)-4,7-O-benzylidene-5-C-hydroxymethyl-1,4-cyclohexanediol

methyl iodide

benzaldehyde dimethyl acetal

(1R,2S,4R)-2-Hydroxymethyl-cyclohexane-1,4-diol

Downstream raw materials:

DL-(1,5/4)-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol

DL-(1,5/4)-1-O-methyl-4-O-p-toluenesulfonyl-5-C-(p-toluenesulfonyloxy)methyl-1,4-cyclohexanediol