Methacrylic Acid → 2-Methyl-2-adamantyl methacrylate

HRID 858915

반응식

HRID 858915 반응식
[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]

참가 물질

6

반응물 4

HCID 4093Methacrylic AcidHCID 14798Sodium HydroxideHCID 1366842-Methylideneadamantane2회HCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 98375662-Methyl-2-adamantyl methacrylate수율 90.8%

시약·촉매·용매 1

HCID 1140Toluene용매3회

반응 조건

온도
5 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-df05f8ba0c784261936ad0e556213ca1
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148363B2

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