Benzoyl chloride → 5-Methyl-2-(propan-2-yl)cyclohexyl benzoate

HRID 2307499Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:12]([O:8][CH:6]1[CH:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:7]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 16666(-)-Menthol

Product 1

HCID 938685-Methyl-2-(propan-2-yl)cyclohexyl benzoate

Procedure

A solution of 1-menthol (1 gram) in benzoyl chloride (1 ml) was stirred at room temperature for 72 hours. This solution yielded menthyl benzoate of 89.5% purity. Further purification of this product through column chromatography resulted to increase in purity level to at least 98.8%. This fraction yielded colourless crystals and confirmed for purity by 1HNMR, 13CNMR, IR and Mass spectra.

Sources & evidence

ORD record: ord-5d3f34200144467db655e0c2dc3f8ff9
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831100B2

Reaction notes

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