Acetyl chloride → 3-Acetoxy-4-pentyloxy-benzaldehyde

HRID 275177노트

반응식

HRID 275177 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:5]=[O:6].C(N(C(C)C)CC)(C)C.[C:25](Cl)(=[O:27])[CH3:26]>C(Cl)Cl.CCOCC>[C:25]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:5]=[O:6])(=[O:27])[CH3:26]

참가 물질

6

반응물 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 132247513-Hydroxy-4-pentyloxybenzaldehyde

생성물 1

HCID 200905923-Acetoxy-4-pentyloxy-benzaldehyde수율 83.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

3-Hydroxy-4-pentyloxy-benzaldehyde (0.750 g., 3.6 mmol, 1 equiv. ) is dissolved in 10 mL of methylene chloride. Diisopropyl ethyl amine (0.840 g., 6.5 mmol, 1.8 equiv. ) is then added, and the mixture is cooled to 0° C. Acetyl chloride (0.340 g., 4.32 mmol, 1.2 equiv. ) dissolved in 2 mL of methylene chloride is added slowly, and the reaction is stirred at 0° C. for 20 min., followed by stirring 30 min. at room temperature. The mixture is diluted with ether, and washed twice with water, dilute HCl, then brine. The organic phase is dried (MgSO4), and evaporated. Trituration with ether affords 3-acetoxy-4-pentyloxy-benzaldehyde (0.750 g., 3.0 mmol, 83%) as a white solid: UVmax (EtOH) 232 nm (ε=17514), 276 nm (ε=12951), 208 nm (ε=10508), 314 nm (ε=10472 ); 1H NMR (300 MHz, CDCl3) δ 9.85 (s, 1H, CHO), 7.45-7.40 (m, 2H, ArH), 6.95 (d, J=8 Hz, 1H, ArH), 4.15 (t, J=7 Hz, 2H, OCH2R), 2.03 (s, 3H, CH3CO), 1.90-1.85 (m, 2H, OCH2CH2R), 1.57-1.40 (m, 4H, pentyl), 0.95 (t, J=7 Hz, 3H, RCH3); 13C NMR (75 MHz, CDCl3) δ 191.07 (C=O), 151.31, 146.17, 130.39, 124.56, 113.99, 110.85, 69.27, 28.67, 28.04, 22.38, 13.96; IR (KBr) 2950, 1750, 1680, 1600, 1580, 1510, 1230, 1250 cm-1 ; MS (DCI) m/e 251 (MH+). Anal. Calcd for C14H18O4 : C, 67.20; H, 7.20. Found: C, 66.92; H, 7.62.

후처리

  1. additionis added slowly
  2. stirringby stirring 30 min. at room temperature
  3. washwashed twice with water, dilute HCl
  4. dry with materialThe organic phase is dried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-77341353b17c42c9afe62df6631c9dad
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391817

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