2-isopropyl-5-methylcyclohexyl phenylacetate synthesis
- Product Name:2-isopropyl-5-methylcyclohexyl phenylacetate
- CAS Number:1154-92-3
- Molecular formula:C18H26O2
- Molecular Weight:274.4
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Yield:1154-92-3 50%
Reaction Conditions:
with 1,8-diazabicyclo[5.4.0]undec-7-ene;lithium bromide in tetrahydrofuran;dichloromethane;
Steps:
2 Transesterification of phenylacetic acid methyl ester to phenylacetic acid-(R) menthyl ester
EXAMPLE 2 Transesterification of phenylacetic acid methyl ester to phenylacetic acid-(R) menthyl ester Following method B, phenylacetic acid methyl ester (751 mg, 5 mmol), LiBr (2.17 g, 25 mmol) and (R)-(-)-menthol (751 mg, 5 mmol) were dissolved in THF/CH2 Cl2 (3:1 v/v, 20 ml). DBU (0.37 ml, 2.5 mmol) was added and the reaction mixture was heated at reflux for several hours. The thin-layer chromatogram (SiO2:pentane/diethyl ether 4:1 v/v) showed that transesterification was not complete after boiling at reflux for 24 hours. Even so, the reaction mixture was hydrolyzed and processed. Flash chromatography (SiO2 pentane diethyl ether 4:1 v/v) showed 691 mg (a 50% yield) of phenylacetic acid-(R)-menthyl ester in the form of an oil substantially pure in 1H-NMR.
References:
US6090913,2000,A
2216-51-5
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$5.00/100mg
101-97-3
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1154-92-3
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