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Sulfuric Acid → 2,4-Dihydroxy benzoic acid tert-butyl ester

HRID 18438
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HRID 18438 반응식
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH2:17]=[C:18]([CH3:20])[CH3:19].C([O-])(O)=O.[Na+]>O1CCOCC1>[C:18]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:2]=1[OH:1])([CH3:20])([CH3:19])[CH3:17]
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참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 14912,4-Dihydroxybenzoic AcidHCID 8255IsobutyleneHCID 516892Sodium Bicarbonate

생성물 1

HCID 217835472,4-Dihydroxy benzoic acid tert-butyl ester

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
-50 °C

실험 절차

To a solution of 2,4-dihydroxy benzoic acid (3.08 g; 20 mmol) in dioxane (50 mL) was added conc. H2SO4 (3 mL) and the solution was cooled to −50° C. Isobutene (40 g) was added, the reaction flask sealed and allowed to warm to room temperature. The reaction mixture was stirred overnight, cooled to −30° C. and pH adjusted to 8 using saturated NaHCO3 (aq). The organic phase was Isolated, dried, evaporated to dryness and purified by column chromatography (SiO2-heptane/EtOAc=4:1) to yield 2.3 g (54%). MS (LC-MS): 209 (MH−).

후처리

  1. customthe reaction flask sealed
  2. temperatureto warm to room temperature
  3. temperaturecooled to −30° C.
  4. customThe organic phase was Isolated
  5. customdried
  6. customevaporated to dryness
  7. custompurified by column chromatography (SiO2-heptane/EtOAc=4:1)
  8. customto yield 2.3 g (54%)

출처 및 근거

ORD 기록
ord-4671f261620a43e7a6758dd6c1540ef9
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741352B2

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