Terephthalaldehyde → 4-(Hydroxymethyl)benzaldehyde

HRID 8901

반응식

HRID 8901 반응식
[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

참가 물질

6

반응물 3

HCID 12173TerephthalaldehydeHCID 195092-PyridinemethanamineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 5563304-(Hydroxymethyl)benzaldehyde수율 78%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2adf7b177715439eb19c5c872418961b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091217B2

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