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Sulfuric Acid → 2-(2-Trifluoromethyl-2-propenoyloxy)-2-methyladamantane

HRID 858913
ノート
印刷プレビュー

反応式

HRID 858913 の反応式
[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:15]=[C:16]1[CH:23]2[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:25][CH:17]1[CH2:18]3)[CH2:22]2.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4]([O:6][C:16]1([CH3:15])[CH:17]2[CH2:25][CH:21]3[CH2:20][CH:19]([CH2:24][CH:23]1[CH2:22]3)[CH2:18]2)=[O:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1366842-Methylideneadamantane2 回HCID 5876942-(Trifluoromethyl)acrylic acid

生成物 1

HCID 113006922-(2-Trifluoromethyl-2-propenoyloxy)-2-methyladamantane収率 93%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒
3 回

反応条件

温度
5 °C

実験手順

A 500 ml flask was flushed with nitrogen to displace the air with nitrogen, and was charged with 70.0 g (0.50 mol) of α-trifluoromethylacrylic acid (supplied from Tosoh F-tech Inc.), 1.0 g (10 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 5° C. Then the content was stirred for 15 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, 133.9 g (yield: 93.0%) of the object 2-methyl-2-adamantyl α-trifluoromethylacrylate 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-5087dbe0678d4eaf81775c0dcbdce07c
出典データセット
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07148363B2

反応ノート

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