p-Toluenesulfonic acid → HCID 23507821, compound

HRID 1377084Notes

Reaction equation

HRID 1377084 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:17](O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:16])[CH2:11][CH2:12][C:13]([O:15][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])=[O:14])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 81931-DodecanolHCID 2721704-(4-nitrophenyl)-4-oxobutanoic acid

Product 1

HCID 23507821HCID 23507821, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-nitrophenyl)-4-oxobutyric acid (0.50 g, 2.2 mmol), 1-dodecanol (5.0 ml, 22 mmol), and p-toluenesulfonic acid (50 mg) in tetrahydrofuran (2.5 ml) was stirred 60 hours at room temperature then heated under reflux for 1.5 hours. Concentration of the reaction mixture in vacuo and purification by chromatography or silica gel (200 g) eluting with methylene chloride:hexane (1.1 to 2:1) followed by filtration of the solid product from a small volume of hexane gave, after drying under high vacuum, dodecyl 4-(4-nitrophenyl)-4-oxobytyrate (0.43 g) as a white solid. 1H NMR (DMSO-66, 300 MHz) δ: 0.86 (t, J=6.5 Hz, 3H, ester CH3), 1.07-1.35 (m, 18H, ester CH2 's), 1.47-1.60 (m, 2H, ester CH2), 2.69 (t, J=6 HZ, 2H, CH2), 3.39 (t, J=6 HZ, 2H, CH2), 4.00 (t, J=6.5 Hz, 2H, ester CH2), 8.22 (d, J=9 Hz, 2H, Ar), 8.36 (d, J=9 Hz, 2H, Ar). Anal. Calculated for C22H33NO5 : C, 67.49; H, 8.50; N, 3.58. Found: C, 67.36; H, 8.54; N, 3.55.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 1.5 hours
  3. customConcentration of the reaction mixture in vacuo and purification by chromatography or silica gel (200 g)
  4. washeluting with methylene chloride
  5. filtrationhexane (1.1 to 2:1) followed by filtration of the solid product from a small volume of hexane
  6. customgave
  7. customafter drying under high vacuum, dodecyl 4-(4-nitrophenyl)-4-oxobytyrate (0.43 g) as a white solid

Sources & evidence

ORD record
ord-27cd183d198246afa2e762b56f91bc58
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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