Sulfuric Acid → 2-Bromomethylphenylacetic acid t-butyl ester

HRID 397475ノート

反応式

HRID 397475 の反応式
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[CH3:18][C:19](=[CH2:21])[CH3:20].C(=O)(O)[O-].[Na+]>O1CCOCC1.COC(C)(C)C>[C:19]([O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][Br:1])([CH3:21])([CH3:20])[CH3:18]

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 12889260[2-(Bromomethyl)phenyl]acetic acid

生成物 1

HCID 590858792-Bromomethylphenylacetic acid t-butyl ester

試薬・触媒・溶媒 2

HCID 15413tert-Butyl methyl ether溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
-15 °C

実験手順

To a solution of 80 g (0.349 mol) 2-bromomethylphenylacetic acid in 700 mL 1,4-dioxane in a 2 L heavy-walled flask was added 84 mL (1.571 mol) concentrated sulfuric acid at ambient temperature. The reaction mixture was chilled to −15° C., and 580 mL isobutylene was condensed directly into the reaction vessel. The sealed pressure flask was shaken mechanically at room temperature for 4 h (the pressure inside the flask rises to ca. 20 psi during this step). The mixture was carefully quenched by slowly pouring it into a 0-5° C. stirred mixture of 1.2 L tert-butyl methyl ether and 336 g (4.0 mol) solid sodium bicarbonate before slow dilution with 1.2 L ice-water. The separated organic phase was washed with 0.8 L brine, dried with sodium sulfate, filtered concentrated in vacuo to give an oil, which was used without further purification.

後処理

  1. customcondensed directly into the reaction vessel
  2. customThe mixture was carefully quenched
  3. additionby slowly pouring it into a 0-5° C.
  4. stirringstirred
  5. washThe separated organic phase was washed with 0.8 L brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an oil, which
  10. customwas used without further purification

出典と根拠

ORDレコード
ord-7e5bab0db56749dea4088df587c46272
出典データセット
uspto-grants-2003_08
特許番号
US06610701B2

反応ノート

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