D-ALPHA BETA-CYCLOHEXYLIDENE-GLYCEROL

Base Information

• Chemical Name: D-ALPHA BETA-CYCLOHEXYLIDENE-GLYCEROL
• CAS No.: 95335-91-4
• Molecular Formula: C9H16O3
• Molecular Weight: 172.224
• Hs Code.: 2932990090
• Mol file: 95335-91-4.mol

Synonyms:(2S)-1,4-Dioxaspiro[4.5]decane-2-methanol;(S)-1,2-O-Cyclohexylideneglycerine;2,3-O-Cyclohexylidene-D-glycerol;(+)-1,4-Dioxaspiro[4.5]decane-2-methanol;(+)-(S)-1,4-Dioxaspiro[4.5]decane-2-methanol;1,4-Dioxaspiro[4.5]decane-2-methanol,(S)-;

Chemical Property of D-ALPHA BETA-CYCLOHEXYLIDENE-GLYCEROL

Chemical Property:

• Vapor Pressure: 0.00396mmHg at 25°C
• Refractive Index: n20/D 1.477(lit.)
• Boiling Point: 248.3 °C at 760 mmHg
• Flash Point: 138.3 °C
• PSA: 38.69000
• Density: 1.13 g/cm³
• LogP: 1.05450
• Storage Temp.: 2-8°C

Purity/Quality:

98%Min ^*data from raw suppliers

D-α,β-Cyclohexylideneglycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: D-α,β-Cyclohexylideneglycerol can be used:As an intermediate in the synthesis of antiarrhythmic oral drugs: (+)- and (?)-mexiletine.As a precursor in the preparation of glycoglycerolipids.As an intermediate in the synthesis of (S)-hydroxymethyl-1,4-benzodioxane, a key intermediate for the preparation of α-adrenergic receptor antagonists, and antidepressant drug doxazosin.

Technology Process of D-ALPHA BETA-CYCLOHEXYLIDENE-GLYCEROL

There total 5 articles about D-ALPHA BETA-CYCLOHEXYLIDENE-GLYCEROL 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:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1,4-dioxaspiro[4.5]decane-2-methanol (95335-91-4) + 3-phenoxy-1,2-propanediol (538-43-2) + phenol (108-95-2,27073-41-2)

Guidance literature:

With 5%-palladium/activated carbon; In neat (no solvent); at 130 ℃; for 24h; Time; Inert atmosphere; Green chemistry;

DOI:10.1039/c2gc36776a

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1,4-dioxaspiro[4.5]decane-2-methanol (95335-91-4) + 3-phenoxy-1,2-propanediol (538-43-2)

Guidance literature:

With oct-1-ene; 5%-palladium/activated carbon; at 130 ℃; for 72h; Inert atmosphere; Sealed tube;

DOI:10.1002/ejoc.201300485

Reference yield:

1,4-dioxaspiro[4.5]decane-2-methanol (95335-91-4) + benzoyl chloride (98-88-4) → (S)-1,4-dioxaspiro<4.5>decane-2-methanol (95335-91-4) + (R)-(1,4-dioxaspiro[4.5]dec-2-yl)methanol (113798-80-4) + (S)-2-benzoyloxymethyl-1,4-dioxaspiro[4.5]decane + (R)-2-benzoyloxymethyl-1,4-dioxaspiro[4.5]decane

Guidance literature:

With 4 A molecular sieve; N-ethyl-N,N-diisopropylamine; (S)-1-methyl-2-[(N-benzyl-N-methylamino)methyl]pyrrolidine; In dichloromethane; N,N-dimethyl-formamide; at -78 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2005.01.034

upstream raw materials:

cyclohexanone

glycerol

benzoyl chloride

Downstream raw materials:

2-(2,4-Dinitro-phenoxymethyl)-1,4-dioxa-spiro[4.5]decane

4-(1,4-Dioxa-spiro[4.5]dec-2-ylmethoxy)-benzonitrile

(1,4-Dioxa-spiro[4.5]dec-2-yl)-methanol

(R)-(1,4-dioxaspiro[4.5]dec-2-yl)methanol

Refernces

• 1、 Sutter, Marc,Lafon, Romain,Raoul, Yann,Metay, Estelle,Lemaire, Marc. "Heterogeneous palladium-catalyzed synthesis of aromatic ethers by solvent-free dehydrogenative aromatization: Mechanism, scope, and limitations under aerobic and non-aerobic conditions". supporting information. p. 5902 - 5916. Retrieved 2013/09/23.
• 2、 Jungen, Manfred,Gais, Hans-Joachim. "Application of pig liver esterase catalyzed transesterification in organic media to the kinetic resolution of glycerol derivatives". . p. 3747 - 3758. Retrieved 2007/10/03.