32226-54-3

Basic information

• Product Name: DL-SOBREROL
• Synonyms: (+-)-p-menth-6-ene-8-diol;3-Cyclohexene-1-methanol, 5-hydroxy-alpha,alpha,4-trimethyl-, trans-(±3-Cyclohexene-1-methanol, 5-hydroxy-alpha,alpha,4-trimethyl-, trans-(.+/-.)-;5-(1-Hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-ol;6,8-Carvomenthenediol, dl-(Z)-;alpha,4-trimethyl-5-hydroxy-alphtrans-(+-)-3-cyclohexene-1-methano;d,l-trans-Sobrerol;dl-(z)-8-carvomenthenediol
• CAS NO: 32226-54-3
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 169.24078
• EINECS: 250-966-4
• Mol File: 32226-54-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 131°C
• Boiling Point: 270.5°C (estimate)
• Appearance: /
• Density: 0.9409 (rough estimate)
• Refractive Index: 1.4494 (estimate)
• CAS DataBase Reference: DL-SOBREROL(CAS DataBase Reference)
• NIST Chemistry Reference: DL-SOBREROL(32226-54-3)
• EPA Substance Registry System: DL-SOBREROL(32226-54-3)

Safety Data

• Hazardous Substances Data: 32226-54-3(Hazardous Substances Data)

Upstream product

• 60661-95-2 1,6-dichloro-p-menthane-2,8-diol 
• 80-56-8 Pinene 
• 110202-13-6 1,2-dibromo-p-menthan-8-ol 
• 80-26-2 terpinyl acetate 
• 17177-64-9 (+/-)-trans-sobrenol diacetate 
• 71697-84-2 (-)-trans-sobrerol 
• 772-36-1 (1R,5R)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-enol 
• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 
• 56423-45-1 (4R,8RS)-8,9-epoxy-p-menth-6-en-2-one 
• 1197-06-4 cis-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol 
• 7664-93-9 sulfuric acid 
• 1197-07-5 (+/-)-trans-carveol 
• 14575-92-9 2,3-epoxy-cis-pinane 
• 56423-45-1 (4S,8RS)-8,9-epoxy-p-menth-6-en-2-one 

Downstream Products

• 7712-46-1 5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enone 
• 137821-91-1 (-)-(1S,5R)-sobrerol 
• 38223-90-4 p-menthane-1,2,6,8-tetraol 
• 17177-64-9 (+/-)-trans-sobrenol diacetate 
• 111323-96-7 C₁₇H₂₄N₂O₃S 
• 127104-12-5 (+/-)-trans-1-methyl-4-<1-methyl-1-(trimethylsiloxy)ethyl>-6-(trimethylsiloxy)cyclohex-1-ene 
• 34182-03-1 (R)-5-(1-hydroxy-1-methylethyl)2-methylcyclohex-2-enone 
• 34182-03-1 (+/-)-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one 
• 71697-84-2 (-)-trans-sobrerol 
• 38235-58-4 trans-sobrerol 
• 98-55-5 terpineol 

Relevant articles and documents

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Biomimetic conversion of α-pinene with H2O2 to sobrerol over V2O5: Dihydroxylation by a peroxo vanadium peracid vectoring gentle synergistic oxidation

In this communication, we report the gentle preparation of sobrerol from dihydroxylation of α-pinene synergistically catalyzed by V2O5-H2O2 under benign conditions. It was proposed that a “peroxo vanadium acid”, VVO(OH)(OOH), was formed by HOO? insertion and proton transfer between V2O5 and H2O2. Theoretical DFT calculations that using the dimer?vanadium peracid as a model of the catalytically active species revealed that peroxo vanadium acid exhibited bifunctional catalytic capabilities resembling epoxidation of α-pinene by peracetic acid and then open-ring hydration with an acetic media.

Mild and selective deprotection of tert -butyl(dimethyl)silyl ethers with catalytic amounts of sodium tetrachloroaurate(III) dihydrate

A simple and mild method for the removal of tert-butyl(dimethyl)silyl (TBS) protecting groups with catalytic amounts of sodium tetrachloroaurate(III) dihydrate is described. The procedure permits selective deprotection of aliphatic TBS ethers in good to excellent yields in the presence of aromatic TBS ethers, aliphatic triisopropylsilyl ethers, aliphatic tert-butyl(diphenyl)silyl ethers, or sterically hindered aliphatic TBS ethers. Additionally, TBS ethers can also be transformed into 4-methoxybenzyl ethers or methyl ethers in one pot by using larger quantities of the catalyst and a higher reaction temperature.