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

HRID 397613

반응식

HRID 397613 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 41438391-(2-Chloroethoxy)-2-methoxybenzene수율 35%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-027af8e544894d078dc39fff3fbae2cd
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610712B2

연결된 노트

불러오는 중…