Ethanol → tert-Butylanisole

HRID 860560ノート

反応式

HRID 860560 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:12]([O-])([O-])=O.[K+].[K+].COS(OC)(=O)=O.CCO>CC(C)=O.CCOCC.O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 4

HCID 702EthanolHCID 6497Dimethyl SulfateHCID 69232-Tert-ButylphenolHCID 11430Potassium Carbonate

生成物 1

HCID 270626tert-Butylanisole収率 78%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

To a suspension of 2-t-butylphenol (20.00 g, 0.133 mol) and K2CO3 (36.80 g, 0.266 mol) in 260 mL of anhydrous acetone was added a neat solution of dimethylsulfate (17.63 g, 0.140 mol) dropwise through a syringe over 5 minute at RT under argon. The resulting thick suspension was stirred over night at RT and 100 mL of EtOH was added. After 1 hour, the mixture was diluted with ether and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine and dried with MgSO4. After filtration, the solvents were removed and dried under high vacuum to give afford 2-t-butylanisole (16.99 g, 78% yield). 1H NMR (300 MHz, CDCl3): δ 1.40 (s, 9H), 3.86 (s, 3H), 6.88–6.96 (m, 2H), 7.18–7.26 (m, 1H), 7.31 (dd, J1=7.5 Hz, J2=1.2 Hz, 1H).

後処理

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried with MgSO4
  4. filtrationAfter filtration
  5. customthe solvents were removed
  6. customdried under high vacuum
  7. customto give

出典と根拠

ORDレコード
ord-1e85675fef6a4618875ab635b878b96e
出典データセット
uspto-grants-2006_12
特許番号
US07153875B2

反応ノート

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