Potassium Permanganate → 2,4,5-Trimethoxybenzaldehyde

HRID 413554노트

반응식

HRID 413554 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:4]=1[CH:5]=CC=O.[O-:17][Mn](=O)(=O)=O.[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:4]=1[CH:5]=[O:17]

참가 물질

4

반응물 2

HCID 516875Potassium PermanganateHCID 540454412,4,5-Trimethoxy cinnamaldehyde

생성물 1

HCID 205252,4,5-Trimethoxybenzaldehyde수율 45.3%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of the 2,4,5-Trimethoxycinnamaldehyde (0.5 g) was treated with KMnO4 (0.5 g) in dry acetone (20 ml). The reaction mixture was left at room temperature for 24 hr, manganese dioxide was filtered off and the solvent was removed. The residue was dissolved in ethyl acetate and washed carefully with 10% NaHCO3, brine, and dried over anhydrous Na2SO4. Evaporation of the solvent afforded a crude solid, which was further recrystallised from water to afford 0.2 g 2,4,5-trimethoxybenzaldehyde as a colorless solid, mp 114° C. (lit. mp 114° C.); IR (film) νmax 1662 (carbonyl group), 1620, 1518, 1481, 1419, 1361, 1300, 1278, 1222, 1199, 1138, 1025, 865 cm−1; 1H NMR δ 10.32 (1H, s, CHO), 7.33 (1H, s, 6H), 6.50 (1H, s, 3H), 3.98 (3H, s, 2-OCH3), 3.93 ((3H, s, 4-OCH3), 3.88 (3H, s, 5-OCH3); 13C NMR δ 187.96 (CHO), 158.60 (C-2), 155.76 (C-4), 143.56 (C-5), 117.35 (C-1), 109.03 (C-6), 56.19 (2-OCH3, 4-OCH3 and 5-OCH3); EIMS m/z 196 [M]+ (100), 181 (49), 150 (32), 125 (33), 110 (23), 69 (37).

후처리

  1. filtrationmanganese dioxide was filtered off
  2. customthe solvent was removed
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed carefully with 10% NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customEvaporation of the solvent
  7. customafforded a crude solid, which
  8. customwas further recrystallised from water

출처 및 근거

ORD 기록
ord-800784b050a942f7b29119eb4c21d45d
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566557B2

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