Hydroquinone → 4-Isopropoxyphenol

HRID 404862

反応式

HRID 404862 の反応式
[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]

参加物

6

反応物 3

HCID 785HydroquinoneHCID 6362Isopropyl iodideHCID 14797Potassium Hydroxide

生成物 1

HCID 820014-Isopropoxyphenol収率 46%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

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),

後処理

  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%)

出典と根拠

ORDレコード
ord-677e80894f0345bebf090fa10f63bd2f
出典データセット
uspto-grants-2014_06
特許番号
US08748627B2

関連ノート

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