p-Toluenesulfonic acid → HCID 23507821, compound

HRID 1884038Notes

Reaction equation

HRID 1884038 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-6, 300 MHz) δ: 0.86 (t, J=6.5 Hz, 3H, esterCH3), 1.07-1.35 (m, 18H, esterCH2's), 1.47-1.60 (m, 2H, esterCH2), 2.69 (t, J=6 Hz, 2H, CH2), 3.39 (t, J=6 Hz, 2H, CH2), 4.00 (t, J=6.5 Hz, 2H, esterCH2), 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-f60ee29bfa984080a2ba2e72ff45c023
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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