Sulfuric Acid → 2-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)

HRID 2308027Notes

Reaction equation

[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].S(=O)(=O)(O)O.[CH2:11]=[C:12]1[CH:19]2[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:21][CH:13]1[CH2:14]3)[CH2:18]2.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:12]1([CH3:11])[CH:13]2[CH2:21][CH:17]3[CH2:16][CH:15]([CH2:20][CH:19]1[CH2:18]3)[CH2:14]2)(=[O:4])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 20 °C

Procedure

A 500 ml flask was flushed with nitrogen to displace the air with nitrogen, and was charged with 36.0 g (0.50 mol) of acrylic acid, 0.5 g (5 mmol) of sulfuric acid and 100 g of toluene. Separately 88.8 g (0.60 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 20° 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, 100.7 g (yield: 91.5%) of the object 2-methyl-2-adamantyl acrylate 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-f2eb7760ff874caa8dcbd77e676813a0
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833462B2

Reaction notes

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