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10399-13-0

10399-13-0 Structure

10399-13-0 Structure
IdentificationMore
[Name]

Methyl cyclohexylphenylglycolate
[CAS]

10399-13-0
[Synonyms]

CYCLOHEXYLMANDELIC ACID METHYL ESTER
METHYL 2-CYCLOHEXYL-2-HYDROXY-PHENYLACETATE
METHYL ALPHA-CYCLOHEXYLMANDELATE
METHYL CYCLOHEXYLPHENYLGLYCOLATE
Methylcyclohexyl mandelate
ALPHA-CYCLOHEXYLMANDELIC ACID METHYL ESTER
methyl 2-hydroxy-2-cyclohexyl-2-phenylacetate
Cyclohexylphenylglycolic acid methyl ester
α-Cyclohexyl-α-hydroxybenzeneacetic acid methyl ester
[EINECS(EC#)]

233-862-3
[Molecular Formula]

C15H20O3
[MDL Number]

MFCD00269807
[Molecular Weight]

248.32
[MOL File]

10399-13-0.mol
Questions And AnswerBack Directory
[Synthesis]

Synthetic route of Methyl cyclohexylphenylglycolate

Under nitrogen, cyclohexane bromide (5.96 g, 36.55 mmol) was added dropwise to a mixture of magnesium chips (0.87 g, 36.25 mmol) and iodine crystals in anhydrous diethyl ether, starting with 1 mL and adding the remainder after the reaction had started, while maintaining gentle reflux. The mixture was stirred at room temperature until all the magnesium was dissolved (1 h). The resulting cyclohexyl magnesium bromide solution was cooled to 0 °C. A solution of 2-methyl 2-oxo-2-phenylacetate (3.0 g, 18.29 mmol) in tetrahydrofuran (20 mL) was added dropwise. The reaction mixture was allowed to reach room temperature and stirred for 2 h.

The mixture was then cooled to 0°C, quenched by slow addition of a saturated ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na₂SO₄, and the solvent was evaporated under reduced pressure to obtain a crude residue, which was purified by silica gel column chromatography (1.5% ethyl acetate in petroleum ether) to give a yellow, viscous Methyl cyclohexylphenylglycolate, liquid (2.6 g, 57%).
Chemical PropertiesBack Directory
[Appearance]

Light Yellow Oil
[Melting point ]

40 °C
[Boiling point ]

170-175 °C(Press: 9 Torr)
[density ]

1.130±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

Chloroform (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

12.19±0.29(Predicted)
[color ]

White to Off-White
[Major Application]

pharmaceutical
[InChI]

1S/C15H20O3/c1-18-14(16)15(17,12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2,4-5,8-9,13,17H,3,6-7,10-11H2,1H3
[InChIKey]

SPTZOODMHSABLY-UHFFFAOYSA-N
[SMILES]

O(C)C(=O)C(O)(C2CCCCC2)c1ccccc1
[CAS DataBase Reference]

10399-13-0(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P280-P301+P312-P302+P352-P305+P351+P338
[WGK Germany ]

WGK 3
[REACH Registrations]

Active
[HS Code ]

2918191350
[Storage Class]

13 - Non Combustible Solids
Hazard InformationBack Directory
[Chemical Properties]

Light Yellow Oil
[Uses]

Methyl 2-Cyclohexyl-2-hydroxyphenylacetate is an impurity of Oxybutynin
[Uses]

Methyl 2-Cyclohexyl-2-hydroxyphenylacetate is an impurity of Oxybutynin (O868525).
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