Terephthalaldehyde → 4-(Hydroxymethyl)benzaldehyde

HRID 899722Notes

Reaction equation

HRID 899722 reaction equation
[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

Participants

6

Reactant 3

HCID 12173TerephthalaldehydeHCID 195092-PyridinemethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 5563304-(Hydroxymethyl)benzaldehydeYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2e52e3766019438686f5c6297f3027ec
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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