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Hydrochloric Acid → 3-[(1-Tert-butoxypropan-2-yl)oxy]propan-1-ol

HRID 1784135
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HRID 1784135 반응식
[OH-].[K+].[OH:3][CH2:4][CH2:5][CH2:6][OH:7].S(O[CH:19]([CH2:21][O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:20])(C1C=CC(C)=CC=1)(=O)=O.Cl>O1CCOCC1>[OH:3][CH2:4][CH2:5][CH2:6][O:7][CH:19]([CH2:21][O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 104421,3-PropanediolHCID 14797Potassium HydroxideHCID 72580834TsOCH(CH3)CH2OC(CH3)3

생성물 1

HCID 1643333-[(1-Tert-butoxypropan-2-yl)oxy]propan-1-ol수율 43.8%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Potassium hydroxide (274.27 g) and HO(CH2)3OH (371.93 g) were added to dioxane (3 L), and then TsOCH(CH3)CH2OC(CH3)3 (700 g) prepared in Example 2-1 was added gradually. The reaction solution was refluxed with heating for 16 hours, allowed to cool, and poured onto ice (500 g), neutralized with 2 N hydrochloric acid, concentrated and filtered to remove the precipitated salt. The filtrate was extracted with dichloromethane (250 mL), and the organic layer was washed with water (500 mL) repeatedly 17 times. The organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated with an evaporator, and the concentrate was purified by silica gel chromatography to give the title compound (203.77 g). The NMR spectrum data of the product were as follows.

후처리

  1. temperatureThe reaction solution was refluxed
  2. temperaturewith heating for 16 hours
  3. temperatureto cool
  4. additionpoured onto ice (500 g)
  5. concentrationconcentrated
  6. filtrationfiltered
  7. customto remove the precipitated salt
  8. extractionThe filtrate was extracted with dichloromethane (250 mL)
  9. washthe organic layer was washed with water (500 mL) repeatedly 17 times
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationthe filtrate was concentrated with an evaporator
  13. customthe concentrate was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-bb577df9e2c347328109835fd6a602b1
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07501540B2

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