D-Psicose → N-(4-Butyl-3-hydroxyphenyl)acetamide

HRID 330779Notes

Reaction equation

HRID 330779 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:13][C:14](=[O:16])[CH3:15])[CH:5]=[CH:6][C:7]=1[CH:8](O)[CH2:9][CH2:10][CH3:11].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>[Pd]>[CH2:8]([C:7]1[CH:6]=[CH:5][C:4]([NH:13][C:14](=[O:16])[CH3:15])=[CH:3][C:2]=1[OH:1])[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 441036D-PsicoseHCID 86684775HCID 86684775, compound

Product 1

HCID 89909N-(4-Butyl-3-hydroxyphenyl)acetamideYield 70%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

N-(3-Hydroxy-4-(1-hydroxybutyl)phenyl)acetamide (184 g) was reduced in 20 g batches by dissolving it in de-oxygenated acetic acid (210 mL) in the presence of 10% Pd/C (7 g) at 60 Psi in a Parr hydrogenator for eleven hrs. Upon completion the reaction was filtered over celite and diluted. The acetic acid was removed in vacuo. The resulting oil was diluted with ethyl acetate and was washed three times with water and once with brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude compound was purified via flash chromatography with 100% ethyl acetate to obtain the title compound in 70% yield (120 g) as a waxy tan solid.

Workup

  1. filtrationUpon completion the reaction was filtered over celite
  2. additiondiluted
  3. customThe acetic acid was removed in vacuo
  4. additionThe resulting oil was diluted with ethyl acetate
  5. washwas washed three times with water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude compound was purified via flash chromatography with 100% ethyl acetate

Sources & evidence

ORD record
ord-ac7dab59db0048078193f6b7c897a97e
Source dataset
uspto-grants-2014_11
Patent number
US08877752B2

Reaction notes

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