Hydroquinone → 4-Isopropoxyphenol

HRID 222642

반응식

HRID 222642 반응식
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].I[CH:10]([CH3:12])[CH3:11].[OH-].[K+]>C(O)C.O>[CH:10]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)([CH3:12])[CH3:11]

참가 물질

6

반응물 3

HCID 785HydroquinoneHCID 6362Isopropyl iodideHCID 14797Potassium Hydroxide

생성물 1

HCID 820014-Isopropoxyphenol수율 46%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of hydroquinone (55.7 g, 0.5 mol) and 2-iodopropane (57.5 g, 0.33 mol) in ethanol was added a solution of potassium hydroxide (78.5 g, 0.5 mol) in water (100 mL). 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 (MgSO4) and filtered. The filtrate was concentrated in vacuo to give over 70 g of crude material, which was triturated with dichloromethane and filtered. The filtrate was concentrated and purified on silica gel (5˜35% ethyl acetate/hexane) 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). 1H NMR (300 MHz, CDCl3) δ ppm 8.31 (d, J=1.84 Hz, 1H) 7.99 (dd, J=8.46, 1.84 Hz, 1H) 7.77 (d, J=9.19 Hz, 1H) 7.20-7.34 (m, 2H) 6.89-7.01 (m, 2H) 4.48-4.62 (m, 1H) 2.65 (s, 3H) 1.37 (d, J=5.88 Hz, 6H). MS m/z (DCI) 405.1 (M+H)+.

후처리

  1. temperatureThe dark brown solution was then refluxed for 16 hours
  2. customEthanol was removed
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give over 70 g of crude material, which
  9. customwas triturated with dichloromethane
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated
  12. custompurified on silica gel (5˜35% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-f95e10e93cbd4c03a61ef024963e3a76
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207350B2

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