Methyl iodide → 1,4-Dimethoxy-2,3,5-trimethyl-benzene

HRID 63805

반응식

HRID 63805 반응식
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6](O)[C:5]([CH3:10])=[CH:4][C:3]=1[OH:11].[C:12](=[O:15])([O-])[O-].[K+].[K+].[CH3:18]I>CCC(C)=O>[CH3:18][O:11][C:3]1[CH:4]=[C:5]([CH3:10])[C:6]([O:15][CH3:12])=[C:7]([CH3:8])[C:2]=1[CH3:1]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12785Trimethylhydroquinone

생성물 1

HCID 109240691,4-Dimethoxy-2,3,5-trimethyl-benzene수율 80%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

반응 조건

온도
65 °C

실험 절차

A 2 L 3-N flask was charged with 2,3,5-trimethyl-benzene-1,4-diol (Ex-1B-1) (50 g, 0.33 mol) and MEK (750 mL) to yield an amber solution. Potassium carbonate (210 g, 1.64 mol) was charged to the solution. After 30 min at RT, MeI (81.2 mL, 1.31 mol) was added to the brown suspension. The reaction mixture was heated to 65° C. for 72 h. After cooling to RT, the reaction mixture was concentrated to dryness by rotary evaporation to give a white paste. The paste was washed with EtOAc (3×300 mL). The EtOAc extracts were combined and concentrated by rotary evaporation. The resulting yellow-brown oil was chromatographed (80:20/Heptanes:EtOAc) to yield 1,4-dimethoxy-2,3,5-trimethyl-benzene (Ex-1B-2) (47.2 g, 80%). 1H NMR (400 MHz, CDCl3) δ (ppm): 6.55 (s, 1H), 3.80 (s, 3H), 3.68 (s, 3H), 2.30 (s, 3H), 2.22 (s, 3H), 2.14 (s, 3H).

후처리

  1. customto yield an amber solution
  2. temperatureAfter cooling to RT
  3. concentrationthe reaction mixture was concentrated to dryness by rotary evaporation
  4. customto give a white paste
  5. washThe paste was washed with EtOAc (3×300 mL)
  6. concentrationconcentrated by rotary evaporation
  7. customThe resulting yellow-brown oil was chromatographed (80:20/Heptanes:EtOAc)

출처 및 근거

ORD 기록
ord-f22cc835cbb4410194837ee083966fe1
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447006B2

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