ChemicalBook CAS DataBase List Methyl cyclohexylphenylglycolate

Methyl cyclohexylphenylglycolate synthesis

12synthesis methods

Product Name:Methyl cyclohexylphenylglycolate
CAS Number:10399-13-0
Molecular formula:C15H20O3
Molecular Weight:248.32

108-85-0
339 suppliers
$5.00/10g

15206-55-0 Synthesis

15206-55-0
500 suppliers
$5.00/10g

542-18-7 Synthesis

542-18-7
369 suppliers
$13.00/25g

10399-13-0
134 suppliers
$49.00/5mg

Yield: 58% (42% was by-product other than the objective product)

Reaction Conditions:

with hydrogenchloride;iodine;magnesium in tetrahydrofuran;toluene

Steps:

C.1 Synthesis of 2-cyclohexyl-2-hydroxy-2-phenylacetic acid by Grignard Method
Comparative Example 1 Synthesis of 2-cyclohexyl-2-hydroxy-2-phenylacetic acid by Grignard Method Magnesium (15.8 g) and iodine (200 mg) were added to tetrahydrofuran (73 g) under a nitrogen atmosphere and the mixture was stirred at about 25° C. for 30 min. Cyclohexyl bromide (4.1 g) was added dropwise, tetrahydrofuran (291.9 g) was added and cyclohexyl chloride (86 g) was added dropwise at 60-70° C. The mixture was stirred at 60-75° C. for 2 h and analyzed by gas chromatography. As a result, the remainder of cyclohexyl chloride was 0.1%. The mixture was cooled to 20-30° C. and Grignard solution was added dropwise to a mixture of methyl benzoylformate (82.1 g) and tetrahydrofran (82 ml) at 6-14° C. The dropwise addition ended in 1 h. The mixture was stirred at the same temperature for 1 h and analyzed by HPLC. As a result, methyl benzoylformate was not detected. Tetrahydrofran was evaporated under reduced pressure at 65-80° C. The evaporated amount was 345 ml. Toluene (164 ml) was added and the mixture was added dropwise at 5-38° C. to 7N hydrochloric acid (215 ml) and partitioned by allowing to stand. The pure yield of methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate in the organic layer was calculated by HPLC external standard method using a reference standard. As a result, yield was 58% (42% was by-product other than the objective product).

References:

Sumika Fine Chemicals Co., Ltd. US2003/13911, 2003, A1

108-85-0
339 suppliers
$5.00/10g

15206-55-0 Synthesis

15206-55-0
500 suppliers
$5.00/10g

10399-13-0
134 suppliers
$49.00/5mg

References