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

HRID 858914

反応式

HRID 858914 の反応式
[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]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 6581Acrylic AcidHCID 14798Sodium HydroxideHCID 1366842-Methylideneadamantane2 回

生成物 1

HCID 112182922-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)収率 91.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒3 回

反応条件

温度
20 °C

実験手順

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, 0.5g (5mmol) 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.

後処理

  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

出典と根拠

ORDレコード
ord-d2d15ec625a2434885f5ac819f94c45d
出典データセット
uspto-grants-2006_12
特許番号
US07148363B2

関連ノート

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