Iodine → 4-Iodo-1,2-dimethoxybenzene

HRID 1165465노트

반응식

HRID 1165465 반응식
[C:1]1([O:9][CH3:10])[C:2](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O:3][CH3:4].[I:11]I>C(O)C>[I:11][C:7]1[CH:8]=[C:1]([O:9][CH3:10])[C:2]([O:3][CH3:4])=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 807Iodine2회HCID 7043Veratrole

생성물 1

HCID 2303074-Iodo-1,2-dimethoxybenzene수율 70%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of veratrole (28.0 ml, 0.22M) in 95% ethanol (75 ml) was heated to 60° C. and, while stirring, was treated with iodine (50 g, 0.197M) and yellow mercuric oxide (30.0 g, 0.1385M). The iodine and mercuric oxide were added alternately in small portions over a period of 1.5 hours. After the addition was complete, the cooled mixture was filtered through Celite and concentrated. The residue was taken up in Et2O and again filtered. The Et2O solution was washed with solutions of sodium thiosulfate, 2N NaOH, saturated NaCl, dried over anhydrous K2CO3 and evaporated. The residue was distilled under reduced pressure to give 40.88 g, bp 110°-112° C. (2 mm) pure 4-iodoveratrole [70% yield, literature: Gutzke et al., J. Org. Chem. 22, 1271 (1957), bp 80°-85° C. (1 mm)]. NMR (CDCl3) δ 3.80 ppm (s, 6H, (2x) OCH3), 6.57 (d, 1H, ArH6), 7.20 (m, 2H, ArH3 and ArH5).

후처리

  1. additionAfter the addition
  2. filtrationthe cooled mixture was filtered through Celite
  3. concentrationconcentrated
  4. filtrationagain filtered
  5. washThe Et2O solution was washed with solutions of sodium thiosulfate, 2N NaOH, saturated NaCl
  6. dry with materialdried over anhydrous K2CO3
  7. customevaporated
  8. distillationThe residue was distilled under reduced pressure

출처 및 근거

ORD 기록
ord-2af6c81698b4443ba07b06c314064473
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04910198

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