Hydrochloric Acid → n-(2-butylphenyl)acetamide

HRID 476954Notes

Reaction equation

HRID 476954 reaction equation
O.O[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:16])[CH3:15])[CH2:4][CH2:5][CH3:6].Cl.[H][H]>[Pd].C(O)C>[CH2:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:16])[CH3:15])[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 19836950HCID 19836950, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 249163n-(2-butylphenyl)acetamideYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 10% (w/w) palladium on carbon (7.8 g, wet with an additional 50% by weight of water) in absolute ethanol (625 ml) containing N-[2-(1-hydroxybutyl)phenyl]acetamide (156 g) was prepared, and concentrated hydrochloric acid (3.2 ml) was added. The mixture was shaken under a positive pressure of about 345,000 Pascals (50 pounds per square inch gauge reading) of hydrogen gas. When hydrogen uptake had ceased (in about 24 hours), the mixture was filtered through diatomaceous earth, and the filtrate was concentrated at reduced pressure to afford 135.3 grams (94% yield) of the title compound as a white solid, m.p. 96.5°-99.5°. This material was used in step (f) without further purification.

Workup

  1. customwas prepared
  2. custom(in about 24 hours)
  3. filtrationthe mixture was filtered through diatomaceous earth
  4. concentrationthe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-81b33d35f0d64e678ca27cea3d29a5b0
Source dataset
uspto-grants-1989_12
Patent number
US04886800

Reaction notes

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