57707-91-2

Basic information

• Product Name: (+)-8-PHENYLMENTHOL
• Synonyms: (+)-8-PHENYLMENTHOL;5-Methyl-2-(2-phenylpropan-2-yl)cyclohexanol
• CAS NO: 57707-91-2
• Molecular Formula: C₁₆H₂₄O
• Molecular Weight: 232.36
• Mol File: 57707-91-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 333.1°C at 760 mmHg
• Flash Point: 138.2°C
• Appearance: /
• Density: 0.999 g/mL at 20 °C(lit.)
• Vapor Pressure: 5.55E-05mmHg at 25°C
• Refractive Index: n20/D 1.531
• Storage Temp.: 2-8°C
• BRN: 5265529
• CAS DataBase Reference: (+)-8-PHENYLMENTHOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-8-PHENYLMENTHOL(57707-91-2)
• EPA Substance Registry System: (+)-8-PHENYLMENTHOL(57707-91-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-8-10
• Hazardous Substances Data: 57707-91-2(Hazardous Substances Data)

Usage

Purification Methods

Dissolve the menthol in toluene, dry (Na2SO4), evaporate and chromatograph it on a silica gel column and eluting with 5% Et2O in pet ether to give an oil with the desired rotation. IR has max 3420cm-1 (OH) with consistent 1H NMR [Corey & Ensley J Org Chem 43 1610 1978, Whitesell et al. Tetrahedron 42 2993 1986, Bednarski & Danishefsky J Am Chem Soc 108 7060 1986].

InChI:InChI=1/C16H24O/c1-12-9-10-14(15(17)11-12)16(2,3)13-7-5-4-6-8-13/h4-8,12,14-15,17H,9-11H2,1-3H3/t12-,14-,15-/m0/s1

Upstream product

• 5949-05-3 (S)-Citronellal 
• 98-09-9 benzenesulfonyl chloride 
• 67-56-1 methanol 
• 126378-69-6 (R)-2-Isobutyl-4-oxo-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 89-82-7 pulegone 
• 100-58-3 phenylmagnesium bromide 
• 205057-17-6 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanone 
• 117109-81-6 (Dimethoxy-phosphoryl)-acetic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 89-79-2 (S)-2-Isopropenyl-5-methyl-cyclohexanol 
• 529-00-0 (S)-isopulegone 
• 3391-90-0 (S)-(-)-pulegone 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 108-86-1 bromobenzene 
• 128797-13-7 (4aR,8aS)-4-Oxo-decahydro-naphthalene-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Downstream Products

• 84658-43-5 Cyclopent-3-ene-1,1-dicarboxylic acid bis-[(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 
• 83587-15-9 (S)-2-Vinyl-cyclopropane-1,1-dicarboxylic acid bis-[(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 
• 83587-15-9 (R)-2-Vinyl-1,1-cyclopropandicarbonsaeure-bis<(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl>ester 
• 120130-28-1 (-)-8-phenylmenthyl glycinate 
• 238746-41-3 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 122449-89-2 (-)-(1S,2R,5S)-1-Chloroacetoxy-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexane 
• 129180-87-6 (-)-8-phenylmenthol phenylcarbamate 
• 129180-87-6 Phenyl-carbamic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 129180-87-6 Phenyl-carbamic acid (1R,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Relevant articles and documents

Diastereoselective photocycloaddition reactions of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furans governed by chiral auxiliaries and hydrogen bonding interactions

By using chiral auxiliaries and hydrogen bonding interactions, we have developed diastereoselective photocycloaddition of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furan derivatives. In photoreactions of (?)-menthyl 2-naphthalenecarboxylate with furan and 3-furanmethanol, respective maximum 48% and 40% diastereomeric excesses (d.e.) are observed. In photoreactions of di-8-phenyl-(?)-menthyl 2,3-naphthalenedicarboxylate with 3-furanmethanol, maximum 67% d.e. is obtained. Use of solvents of low polarity, low temperatures and low furan concentration leads to increased diastereoselectivities. Variable-temperature (VT) NMR and fluorescence quenching studies indicate that hydrogen bonding interactions between the carbonyl oxygen of naphthalenecarboxylic acid esters and the OH group in 3-furanmethanol take place in both the ground and excited states. The results of computational studies show that geometries of C2 symmetric naphthalenedicarboxylate reactants are important in governing the high diastereoselectivity in the photoreactions of 2,3-naphthalenedicarboxylates.

Asymmetric Synthesis of 2-Alkyl(Aryl)-2,3-dihydro-4-pyridones by Addition of Grignard Reagents to Chiral 1-Acyl-4-methoxypyridinium Salts

Grignard addition to a chiral 1-acyl-4-methoxypyridinium salt provides synthetically useful 2-alkyl(aryl)-2,3-dihydro-4-pyridones in high diastereomeric excess.

SYNTHESIS OF OPTICALLY ACTIVE 3-OXA-CARBACYCLIN PRECURSORS FEATURING ASYMMETRIC HORNER-EMMONS REACTION

An enantiselective synthesis of 5 is described.Asymmetric Horner-Emmons reactions with the chiral phosphonate 6 are key steps in the synthesis of the allylic alcohols E-8 and E-11 from the ketones 5 and 9, respectively.