p-Toluenesulfonic acid → HCID 22387700, compound

HRID 1072708Notes

Reaction equation

HRID 1072708 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][C:12](=O)[CH3:13])=[CH:5][CH:4]=1.[CH2:16]([NH2:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:16]([N:28]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 13583DodecylamineHCID 114698111-(4-Methoxyphenyl)pentane-1,4-dione

Product 1

HCID 22387700HCID 22387700, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(4-methoxyphenyl)-1,4-pentanedione (3.00 g, 14.5 mol), dodecylamine (3.24 g, 17.5 mmol) and p-toluenesulfonic acid (150 mg, 0.871 mmol) in toluene (100 ml) was refluxed for 10 hours under heating using Dean-Stark's apparatus. The insoluble matter was filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the object compound as an oily substance. 4.01 g (yield: 78%)

Workup

  1. temperatureunder heating
  2. filtrationThe insoluble matter was filtered out
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)
  5. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-37faa30c7b6d4e35bad0e0084cbdf770
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

Loading…