(R)-(-)-Hexahydromandelic acid

Base Information

• Chemical Name: (R)-(-)-Hexahydromandelic acid
• CAS No.: 53585-93-6
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• Hs Code.: 2918199090
• European Community (EC) Number: 889-842-5
• Nikkaji Number: J58.786I
• Mol file: 53585-93-6.mol

Synonyms:53585-93-6;(R)-(-)-Hexahydromandelic acid;(R)-2-Cyclohexyl-2-hydroxyacetic acid;(2R)-2-cyclohexyl-2-hydroxyacetic acid;(R)-hexahydromandelic acid;SCHEMBL503695;RRDPWAPIJGSANI-SSDOTTSWSA-N;MFCD00009824;(R)-2-Cyclohexyl-2-hydroxyaceticacid;AS-63269;(r)-(-)-2-cyclohexyl-2-hydroxyacetic acid;CS-0204305;A50840;EN300-6768410;(R)-(-)-Hexahydromandelic acid, 98%, optical purity ee: 99% (GLC)

Chemical Property of (R)-(-)-Hexahydromandelic acid

Chemical Property:

• Vapor Pressure: 2.8E-05mmHg at 25°C
• Melting Point: 127-129 °C
• Refractive Index: 1.508
• Boiling Point: 319.3 °C at 760 mmHg
• PKA: 3.86±0.11(Predicted)
• Flash Point: 161.1 °C
• PSA: 57.53000
• Density: 1.178 g/cm³
• LogP: 1.01220
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

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

(R)-(?)-Hexahydromandelic acid 98%, optical purity ee: 99% (GLC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(CC1)C(C(=O)O)O
• Isomeric SMILES: C1CCC(CC1)[C@H](C(=O)O)O
• Uses: (R)-(?)-Hexahydromandelic acid can be used:As an intermediate in the synthesis of antimycobacterial compound pyridomycin analogs.As a model α-hydroxy acid compound in the chirality sensing studies of organic probes using circular dichroism technique.As a starting material in the synthesis of chiral ionic liquids, which are applicable as chiral solvents in asymmetric synthesis and as chiral stationary phases in chromatographic separations.

Technology Process of (R)-(-)-Hexahydromandelic acid

There total 62 articles about (R)-(-)-Hexahydromandelic acid 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%

phosphoric acid dicyano-cyclohexyl-methyl ester diethyl ester → 2-cyclohexyl-2-hydroxyacetic acid (4442-94-8,10498-47-2,53585-93-6,61475-31-8)

Guidance literature:

With hydrogenchloride; for 14h; Heating;

DOI:10.1016/S0040-4039(98)02099-1

Reference yield: 92.0%

(R)-Mandelic Acid (611-71-2) → (R)-(-)-hexahydromandelic acid (53585-93-6)

Guidance literature:

With rhodium contaminated with carbon; hydrogen; acetic acid; In methanol; at 20 ℃; for 8h; under 72402.6 Torr;

Reference yield: 90.0%

(R)-S-ethylthio cyclohexylglycolate (157982-33-7) → (R)-(-)-hexahydromandelic acid (53585-93-6)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(97)01010-7

upstream raw materials:

(R)-Mandelic Acid

(R)-2-cyclohexyl-2-hydroxyacetonitrile

ethyl (R)-2-hydroxy-2-cyclohexylacetate

(R)-S-ethylthio cyclohexylglycolate

Downstream raw materials:

benzyl 2-cyclohexyl-2-hydroxyethanoate

N-(3-benzyloxyphenyl)-2-cyclohexyl-2-hydroxyacetamide

C₁₈H₃₂N₂O₄

2-cyclohexyl-2-hydroxy-N-(4-imidazol-1-ylphenyl)acetamide

Refernces

• 1、 Guyon, Hélène,Boussonnière, Anne,Castanet, Anne-Sophie. "Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation". . p. 4949 - 4957. Retrieved 2017/05/12.
• 2、 Mo, Kilwoong,Kang, Soon Bang,Kim, Youseung,Lee, Yong Sup,Lee, Jae Wook,Keum, Gyochang. "Chemo- And stereoselective reduction of β-keto-α-oximino nitriles by using baker's yeast". . p. 1137 - 1143. Retrieved 2015/02/19.