Terephthalaldehyde → 4-(Hydroxymethyl)benzaldehyde

HRID 8901

反応式

HRID 8901 の反応式
[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

反応物 3

HCID 12173TerephthalaldehydeHCID 195092-PyridinemethanamineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 5563304-(Hydroxymethyl)benzaldehyde収率 78%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

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) δ 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

  1. filtrationThe mixture was filtered through celite
  2. washthe cake washed with methanol
  3. customthe solvent from the eluent removed in vacuo
  4. 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-2adf7b177715439eb19c5c872418961b
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

関連ノート

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