Diethyl Ether → 2,5-Bis(hexyloxy)-4-(hydroxymethyl)benzaldehyde

HRID 1528560ノート

反応式

HRID 1528560 の反応式
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]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 867124912-(4-Methylbenzoxazolyl)-5-(hydroxylmethyl)-1,4-bis(hexyloxy)benzeneHCID 178479088HCID 178479088、化合物

生成物 1

HCID 867124922,5-Bis(hexyloxy)-4-(hydroxymethyl)benzaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  1. washThe yellow and highly fluorescent product was then washed off the column with CH2Cl2

出典と根拠

ORDレコード
ord-d0966c7f4ae44c7cbeecfb65c30c6858
出典データセット
uspto-grants-2015_07
特許番号
US09090602B2

反応ノート

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