p-Toluenesulfonic acid → HCID 71245667, 화합물

HRID 575500노트

반응식

HRID 575500 반응식
[CH3:1][O:2][C:3]1[C:4]2[S:20][CH:19]=[CH:18][C:5]=2[C:6]2[CH:7]=[C:8]([O:16][CH3:17])[C:9]3[S:15][CH:14]=[CH:13][C:10]=3[C:11]=2[CH:12]=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.[CH2:32]([CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])CO)[CH2:33][CH2:34][CH3:35].[CH3:45][CH2:46][CH2:47][CH2:48]CC>CCCCCC.ClCCl>[CH2:45]([CH:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:21][CH3:31])[CH2:17][O:16][C:8]1[C:9]2[S:15][CH:14]=[CH:13][C:10]=2[C:11]2[CH:12]=[C:3]([O:2][CH2:1][CH:36]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:4]3[S:20][CH:19]=[CH:18][C:5]=3[C:6]=2[CH:7]=1)[CH2:46][CH2:47][CH3:48]

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 8058HexaneHCID 198002-Butyl-1-octanolHCID 71245552HCID 71245552, 화합물

생성물 1

HCID 71245667HCID 71245667, 화합물수율 68.5%

시약·촉매·용매 1

HCID 21226440Methylenechloride Hexane용매

반응 조건

온도
180 °C

실험 절차

Compound 7 (1.80 g, 6.0 mmol), 1.14 g (6.0 mmol) of toluene-4-sulfonic acid (CH3C6H4SO3H.H2O), and 35 mL of 2-butyloctanol were added into a 250 mL 3-neck flask equipped with a ondenser. The system was heated at 180° C. overnight under argon before the mixture was cooled down to room temperature. Hexane (200 mL) was added and the organic layer was washed with saturated NaHCO3 before the solvent was removed under vacuum. Excess 2-butyloctanol was distilled out under vacuum. Column chromatography (silica gel) with an eluent of hexane/dichloromethane (v/v, 100/4) yielded product BB-4 as a colorless liquid (2.5 g, ˜68.5% yield). 1H NMR (CDCl3, 500 MHz): δ 7.96 (d, 2H, J=5.5 Hz), δ 7.60 (d, 2H, J=5.5 Hz), δ 7.50 (s, 2H), δ 4.23 (d, 4H, J=5.5 Hz), δ 1.99 (m, 2H), δ 1.33 (m, 32H), δ 0.96 (t, 6H, J=7.0 Hz), δ 0.90 (t, 6H, J=7.0 Hz).

후처리

  1. customequipped with a ondenser
  2. temperaturewas cooled down to room temperature
  3. washthe organic layer was washed with saturated NaHCO3 before the solvent
  4. customwas removed under vacuum
  5. distillationExcess 2-butyloctanol was distilled out under vacuum

출처 및 근거

ORD 기록
ord-bf230322e9ab46d48f7cc0fca0d8ab85
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035004B2

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