Sulfuric Acid → 2-Ethyl-2-methacryloyloxyadamantane

HRID 2122065

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

70 g of 2-ethyl-2-adamantanol was dissolved in toluene, 1 g of p-toluenesulfonic acid was added, and water was removed by distillation by use of a Dean and Stark dehydrator under heating so as to obtain 2-ethylideneadamantane. To 50 g of the obtained 2-ethylideneadamantane, 500 g of methacrylic acid and 0.1 ml of concentrated sulphuric acid were added, and the resulting mixture was heated at 80° C. for 5 hours. After hexane was added to the obtained reaction mixture, the mixture was washed with water, a 5% sodium hydroxide solution, and water in turn, and it was confirmed that the pH of an aqueous phase became 8. After the washed organic phase was concentrated, unreacted 2-ethylideneadamantane was partially removed by sublimation so as to obtain crude 2-ethyl-2-adamantyl methacrylate containing 80% by weight of 2-ethyl-2-adamantyl methacrylate.

Workup

washthe mixture was washed with water
concentrationAfter the washed organic phase was concentrated
customunreacted 2-ethylideneadamantane was partially removed by sublimation so as

Sources & evidence

ORD record: ord-1a966fb6ef364f7798394a9b6e8b065b
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696595B2

Linked notes

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