Hydroquinone → 4-Isopropoxyphenol

HRID 404862

반응식

HRID 404862 반응식
[OH-].[K+].[C:3]1([CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1)[OH:4].I[CH:12]([CH3:14])[CH3:13]>O.C(O)C>[CH:12]([O:4][C:3]1[CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1)([CH3:14])[CH3:13]

참가 물질

6

반응물 3

HCID 785HydroquinoneHCID 6362Isopropyl iodideHCID 14797Potassium Hydroxide

생성물 1

HCID 820014-Isopropoxyphenol수율 46%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

A solution of potassium hydroxide (78.5 g, 0.5 mol) in water (100 mL) was added to a solution of hydroquinone (55.7 g, 0.5 mol) and 2-iodopropane (57.5 g, 0.33 mol) in ethanol. The dark brown solution was then refluxed for 16 hours Ethanol was removed and the aqueous phase was acidified with 2N HCl and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated to give over 70 g of crude material, which was triturated with dichloromethane and filtered. The filtrate was concentrated and purified on silica gel (ethyl acetate/hexane, 5˜35%) to give 23.0 g of product as a brown oil (46% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.30 (d, J=5.88 Hz, 6H) 4.30-4.50 (m, 1H) 4.78 (s, 1H) 6.66-6.86 (m, 4H), MS (ESI): m/z 151 (M−H),

후처리

  1. customwas removed
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customto give over 70 g of crude material, which
  8. customwas triturated with dichloromethane
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. custompurified on silica gel (ethyl acetate/hexane, 5˜35%)

출처 및 근거

ORD 기록
ord-677e80894f0345bebf090fa10f63bd2f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748627B2

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