Guaiacol → 1-(2-Chloroethoxy)-2-methoxybenzene

HRID 397613

反応式

HRID 397613 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].Br[CH:11]([Cl:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:13][CH2:11][CH2:12][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

参加物

5

反応物 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 116541-Bromo-1-chloroethane

生成物 1

HCID 41438391-(2-Chloroethoxy)-2-methoxybenzene収率 35%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

To a solution of 2-methoxyphenol (14.4 g, 116 mmol) in 2-butanone (200 mL) was added bromochloroethane (69.0 g, 480 mmol) followed by the addition of potassium carbonate (40.0 g, 280 mmol). The reaction mixture was mechanically stirred and heated to reflux for 24 h, then cooled to room temperature. The solids were filtered off and the solvent was removed under vacuum. The residue was dissolved in diethyl ether and washed with 10% of NaOH, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by silica gel column chromatography (25% EtOAc/hexane) afforded 7.55 g (35%) of a solid: mp 36-38°C. (Lit.2 41-43° C,); 1H NMR (DMSO, 400 MHz), 3.75 (s, 3H), 3.91 (dd, 2H), 4.20 (dd, 2H), 6.86-6.99 (m, 4H); MS (EI) m/z 186 (M+).

後処理

  1. temperatureheated
  2. temperatureto reflux for 24 h
  3. filtrationThe solids were filtered off
  4. customthe solvent was removed under vacuum
  5. dissolutionThe residue was dissolved in diethyl ether
  6. washwashed with 10% of NaOH
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel column chromatography (25% EtOAc/hexane)

出典と根拠

ORDレコード
ord-027af8e544894d078dc39fff3fbae2cd
出典データセット
uspto-grants-2003_08
特許番号
US06610712B2

関連ノート

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