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

HRID 858913
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HRID 858913 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1366842-Methylideneadamantane2회HCID 5876942-(Trifluoromethyl)acrylic acid

생성물 1

HCID 113006922-(2-Trifluoromethyl-2-propenoyloxy)-2-methyladamantane수율 93%

시약·촉매·용매 1

HCID 1140
Toluene
용매
3회

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온도
5 °C

실험 절차

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.

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-5087dbe0678d4eaf81775c0dcbdce07c
출처 데이터셋
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07148363B2

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