Terephthalaldehyde → 4-(Hydroxymethyl)benzaldehyde
反応式
[CH:1]1[C:6]([CH:7]=[O:8])=[CH:5][CH:4]=[C:3]([CH:9]=[O:10])[CH:2]=1.NCC1C=CC=CN=1.[H][H]>[Pd].CO>[OH:10][CH2:9][C:3]1[CH:2]=[CH:1][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1参加物
6
実験手順
Terephthaldicarboxaldehyde (30.02 g, 224 mmol), methanol (200 mL), palladium on activated carbon, (10%, 3.02 g) and 2-(aminomethyl)pyridine (2.3 mL, 22 mol, 0.01 mol equiv) were combined in a hydrogenation vessel and the reaction mixture was shaken on a Parr hydrogenator for 2.5 hours at 40 psi of hydrogen. The mixture was filtered through celite, the cake washed with methanol and the solvent from the eluent removed in vacuo. Purification of the crude product by column chromatography on silica gel (EtOAc/Hexanes, 1:1) afforded the title compound (23.8 g, 78%) as a white solid. 1H NMR (CDCl3) □ 4.80 (s, 2H), 7.53 (d, 2H, J=9 Hz), 7.87 (d, 2H, J=9 Hz), 10.00 (s, 1H).
後処理
- filtrationThe mixture was filtered through celite
- washthe cake washed with methanol
- customthe solvent from the eluent removed in vacuo
- customPurification of the crude product by column chromatography on silica gel (EtOAc/Hexanes, 1:1)
出典と根拠
- ORDレコード
- ord-6cf759bc757143e7bba62c72bc8bb078
- 出典データセット
- uspto-grants-2006_08
- 特許番号
- US07084155B2
反応ノート
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