4-Hydroxybenzaldehyde → 4-Formylphenyl 4-(decyloxy)benzoate

HRID 417777

반응식

HRID 417777 반응식
[OH-].[K+].[CH2:3]([O:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].OC1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=1.C(N(CC)CC)C>CCO.CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:3]([O:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:20][C:21]2[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=2)=[O:19])=[CH:22][CH:23]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

참가 물질

8

반응물 4

HCID 1264-HydroxybenzaldehydeHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 3574987Methyl 4-(decyloxy)benzoate

생성물 1

HCID 133211564-Formylphenyl 4-(decyloxy)benzoate

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 702Ethanol용매HCID 6344Dichloromethane용매

실험 절차

KOH (3.78 g, 67.6 mmol) was added to a solution of 1 (12.0 g, 41.0 mmol) dissolved in 250 mL of hot EtOH, and the mixture was refluxed for 24 hours. The solvent was filtered off, and following drying over P2O5 the white solid was suspended in 300 mL of toluene, and refluxed with oxalyl chloride (13.4 mL, 158.54) for 6 hours. Volatile components were removed, the yellow solid was taken in CH2Cl2 (100 mL), and added to a stirred solution containing p-hydroxybenzaldehyde (5.26 g, 43.1), triethylamine (36 mL, 0.261 mol), and DMAP (0.28 g, 2.3 mmol) in CH2Cl2 (100 mL). The mixture was let to stir at room temperature for three hours, and then heated to reflux for twelve hours. Following cooling to room temperature, the organic layer was washed with 1 M HCl (2×100 mL), and then distilled water (100 mL). The solvent was removed, and the product was obtained as an off-white solid following recrystallization from ethanol. Yield (8.5 g, 54%). 1H NMR: δH (CDCl3; 300 MHz): 0.91 (3 H, t, 3J=6.8 Hz, CH3), 1.21-1.58 (14 H, m, CH2), 1.85 (2 H, m, O—CH2—CH2), 4.07 (2 H, t, 3J=6.5 Hz, O—CH2), 7.00 (2 H, d, 3J=9.0 Hz, Ar—H), 7.42 (2 H, d, 3J=8.5 Hz, Ar—H), 7.98 (2 H, d, 3J=8.6 Hz, Ar—H), 8.16 (2 H, d, 3J=9.0 Hz, Ar—H), 10.03 (1 H, s, COH). 13C NMR: δC (CDCl3; 75 MHz): 14.5, 23.1, 26.4, 29.5, 29.7, 29.8, 30.0, 32.3, 68.8, 114.8, 121.2, 123.0, 131.6, 132.8, 134.3, 156.3, 164.3, 164.6, 191.4.

후처리

  1. temperaturethe mixture was refluxed for 24 hours
  2. filtrationThe solvent was filtered off
  3. dry with materialfollowing drying over P2O5 the white solid
  4. temperaturerefluxed with oxalyl chloride (13.4 mL, 158.54) for 6 hours
  5. customVolatile components were removed
  6. additionadded to a stirred solution
  7. temperatureheated
  8. temperatureto reflux for twelve hours
  9. temperatureFollowing cooling to room temperature
  10. washthe organic layer was washed with 1 M HCl (2×100 mL)
  11. customThe solvent was removed
  12. customthe product was obtained as an off-white solid following recrystallization from ethanol
  13. customYield (8.5 g, 54%)

출처 및 근거

ORD 기록
ord-32ce7744e54545d8b183b38f8e751e20
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08092712B2

연결된 노트

불러오는 중…