Methacrylic Acid → 2-Methyl-2-adamantyl methacrylate

HRID 2308028Notes

Reaction equation

[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:19]=[C:20]1[CH:27]2[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:29][CH:21]1[CH2:22]3)[CH2:26]2.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:6][C:20]1([CH3:19])[CH:21]2[CH2:29][CH:25]3[CH2:24][CH:23]([CH2:28][CH:27]1[CH2:26]3)[CH2:22]2)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

Conditions

Temperature: 5 °C

Procedure

A 500 ml flask was flushed with nitrogen to displace the air with nitrogen, and was charged with 43.0 g (0.50 mol) of methacrylic acid, 0.95 g (5 mmol) of p-toluenesulfonic acid monohydrate (supplied by Wako Pure Chem. Ind. Ltd.) and 100 g of toluene. Separately 74.0 g (0.50 mol) of 2-methyleneadamantane, prepared by the same procedures as described in Reference Example 1, was dissolved in 100 g of toluene. The obtained solution of 2-methyleneadamantane 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 5° C. Then the content was stirred for 5 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, 106.2 g (yield: 90.8%) of the object 2-methyl-2-adamantyl 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-7faa9bff0c6945f7928edc2205b338fc
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833462B2

Reaction notes

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