Diethyl Ether → 2,5-Bis(hexyloxy)-4-(hydroxymethyl)benzaldehyde
반응식
CC1C2N=[C:9]([C:11]3[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:14]([CH2:24][OH:25])=[CH:13][C:12]=3[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[O:10]C=2C=CC=1.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.[Cr](Cl)([O-])(=O)=O.CCOCC>C(Cl)Cl>[CH2:27]([O:26][C:12]1[CH:13]=[C:14]([CH2:24][OH:25])[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:11]=1[CH:9]=[O:10])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]참가 물질
실험 절차
A solution of 2-(4-methylbenzoxazolyl)-5-(hydroxylmethyl)-1,4-bis(hexyloxy)benzene (1.99 g, 4.53 mmol) in CH2Cl2 (10 mL) was added dropwise to a stirred solution of freshly prepared pyridium chlorochromate (PCC) (1.46 g, 6.80 mmol) in CH2Cl2 (100 mL) at room temperature. Anhydrous Et2O (100 mL) was added, and the mixture was stirred for an additional 2 h. The reaction mixture was then directly transferred onto the top of a short silica gel column. The yellow and highly fluorescent product was then washed off the column with CH2Cl2, giving 2,5-bis(hexyloxy)-4-(hydroxymethyl)benzaldehyde in 86.9% (1.72 g). The product (mp. 48-50° C.) had the following spectral properties. 1H NMR (CDCl3, 300 MHz, δ): 10.53 (s, 1H, —CHO), 7.78 (s, 1H), 7.48 (s, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.26 (dd, J=7.8 Hz, J=7.8 Hz, 1H), 7.17 (d, J=7.2 Hz, 1H), 4.18 (t, J=6.6 Hz, 2H), 4.12 (t, J=6.0 Hz, 2H), 2.68 (s, 3H), 1.87 (q, J=6.3 Hz, 4H), 1.54 (m, 4H), 1.35 (m, 8H), 0.90 (m, 6H). IR(KBr): 1684 cm−1, 1609.5 cm−1, 1534.6 cm−1.
후처리
- washThe yellow and highly fluorescent product was then washed off the column with CH2Cl2
출처 및 근거
- ORD 기록
- ord-d0966c7f4ae44c7cbeecfb65c30c6858
- 출처 데이터셋
- uspto-grants-2015_07
- 특허 번호
- US09090602B2
반응 노트
불러오는 중…