Methyl cyclohexylphenylglycolate

Methyl cyclohexylphenylglycolate - Names and Identifiers

Name	Methyl cyclohexylphenylglycolate
Synonyms	Methylcyclohexyl mandelate METHYL ALPHA-CYCLOHEXYLMANDELATE METHYL CYCLOHEXYLPHENYLGLYCOLATE Methyl cyclohexylphenylglycolate CYCLOHEXYLMANDELIC ACID METHYL ESTER ALPHA-CYCLOHEXYLMANDELIC ACID METHYL ESTER Cyclohexylphenylglycolic acid methyl ester METHYL 2-CYCLOHEXYL-2-HYDROXY-PHENYLACETATE methyl 2-hydroxy-2-cyclohexyl-2-phenylacetate
CAS	10399-13-0
EINECS	233-862-3

Methyl cyclohexylphenylglycolate - Physico-chemical Properties

Molecular Formula	C15H20O3
Molar Mass	248.32
Density	1.130±0.06 g/cm3(Predicted)
Melting Point	40 °C
Boling Point	170-175 °C(Press: 9 Torr)
Solubility	Chloroform (Slightly), Methanol (Slightly)
Appearance	Solid
Color	White to Off-White Waxy to
pKa	12.19±0.29(Predicted)
Storage Condition	Sealed in dry,Room Temperature
Use	Application 2-cyclohexyl-2-hydroxyphenylacetic acid methyl ester is an organic intermediate, it has been reported that it can be prepared from bromocyclohexane and 2-oxo-2-phenylacetic acid -2-methyl ester or benzoyl formate and cyclohexene as starting materials, and can be used in laboratory research and development process and chemical production process.

Methyl cyclohexylphenylglycolate - Risk and Safety

HS Code

2918191350

Methyl cyclohexylphenylglycolate - Upstream Downstream Industry

Raw Materials

Cyclohexylboronic acid
Potassium cyclohexyltrifluoroborate
Methyl benzilate
IODOCYCLOHEXANE
Methyl DL-mandelate
Chlorocyclohexane
Bromocyclohexane
Methyl benzoylformate
CYCLOHEXYLMAGNESIUM BROMIDE
Iodomethane
(TRIMETHYLSILYL)DIAZOMETHANE

Methyl cyclohexylphenylglycolate - Preparation

Under nitrogen, bromocyclohexane (5.96g,36.55 mmol) is added dropwise to the anhydrous ether mixture of magnesium chips (0.87g,36.25 mmol) and iodine crystals, first 1 mL is added, and the rest is added after the start of the reaction, while maintaining mild reflux. Stir the mixture at room temperature until all magnesium is dissolved (1 hour). The cyclohexylmagnesium bromide solution thus obtained was cooled to 0°C. Tetrahydrofuran (20mL) solution of 2-oxo-2-phenylacetic acid (3.0g,18.29mmol) was added dropwise. The reaction mixture was allowed to reach room temperature and stirred for 2 hours. It was then cooled to 0°C, quenched by slowly adding a saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and brine, dried by Na2SO4, and the solvent was evaporated under reduced pressure to give a crude residue, which was purified by silica gel column chromatography (1.5% ethyl acetate in petroleum ether) to obtain yellow viscous 2-cyclohexyl-2-hydroxyphenylacetate methyl, liquid (2.6g,57%).

Last Update：2024-04-10 22:29:15

Methyl cyclohexylphenylglycolate - Reference Information

application

2-cyclohexyl -2-hydroxyphenylacetic acid methyl ester is an organic intermediate. It is reported in the literature that it can be prepared from bromocyclohexane and 2-oxo-2-phenylacetic acid -2-methyl ester or benzoformate and cyclohexene as starting materials, it can be used in laboratory research and development process and chemical production process.

Preparation

Under nitrogen, bromocyclohexane (5.96g,36.55 mmol) is added dropwise to the anhydrous ether mixture of magnesium chips (0.87g,36.25 mmol) and iodine crystals, 1 mL is added first, and the rest is added after the reaction starts while maintaining mild reflux. Stir the mixture at room temperature until all magnesium is dissolved (1 hour). The cyclohexylmagnesium bromide solution thus obtained was cooled to 0°C. Tetrahydrofuran (20mL) solution of 2-oxo-2-phenylacetic acid (3.0g,18.29mmol) was added dropwise. The reaction mixture was allowed to reach room temperature and stirred for 2 hours. It was then cooled to 0°C, quenched by slowly adding a saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and salt water, dried by Na2SO4, and the solvent was evaporated under reduced pressure to give a crude residue, which was purified by silica gel column chromatography (ethyl 1.5% acetate in petroleum ether) to obtain yellow viscous 2-cyclohexyl-2-hydroxyphenylacetate methyl, liquid (2.6g,57%).

Last Update：2024-04-09 21:11:58