Sulfuric Acid → 1-ethylcyclohexyl methacrylate

HRID 2308029Notes

Reaction equation

[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].S(=O)(=O)(O)O.[CH2:12]([C:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=1)[CH3:13].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:6][C:14]1([CH2:12][CH3:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

Conditions

Temperature: 30 °C

Procedure

A 500 ml flask was flushed with nitrogen to displace the air with nitrogen, and was charged with 43.0 g (0.5 mol) of methacrylic acid, 0.5 g (5 mmol) of sulfuric acid and 100 g of toluene. Separately 110.2 g (1.0 mol) of 1-ethylcyclohexene, prepared by the same procedures as described in Reference Example 3, was dissolved in 100 g of toluene. The obtained solution of 1-ethylcyclohexene in toluene was dropwise added to the content in the flask over a period of about 3 hours, while the content was maintained at a reaction temperature of about 30° C. Then the content was stirred for 15 hours at the same temperature. After completion of the reaction, the residual catalyst was neutralized by adding 40.0 g (50 mmol) of a 5% aqueous sodium hydroxide solution, and the neutralized liquid was washed with an aqueous saturated sodium chloride solution. The thus-obtained organic phase was subjected to column chromatography, and further, analyzed by NMR and mass spectrometry. Thus, 68.6 g (yield: 69.9%) of the object 1-ethylcyclohexyl methacrylate was obtained.

Workup

customA 500 ml flask was flushed with nitrogen
customAfter completion of the reaction
washthe neutralized liquid was washed with an aqueous saturated sodium chloride solution

Sources & evidence

ORD record: ord-4cf8a06265904f65b5aaa52426c8fc81
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833462B2

Reaction notes

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