Hydroquinone → 4-Isopropoxyphenol

HRID 222642ノート

反応式

HRID 222642 の反応式
[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]

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HCID 962Water溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-f95e10e93cbd4c03a61ef024963e3a76
出典データセット
uspto-grants-2012_06
特許番号
US08207350B2

反応ノート

読み込み中…