Water → 4-(4-nitrophenyl)-4-oxobutanoic acid

HRID 1884037Notes

Reaction equation

HRID 1884037 reaction equation
C([O:3][C:4]([CH:6]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:14])C(OCC)=O)=[O:5])C.S(=O)(=O)(O)O.O>C(O)(=O)C.O>[N+:21]([C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH2:12][CH2:6][C:4]([OH:5])=[O:3])=[CH:20][CH:19]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 23507919HCID 23507919, compound

Product 1

HCID 2721704-(4-nitrophenyl)-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of ethyl 2-ethoxycarbonyl-4-(4-nitrophenyl)-4-oxobutyrate (6.2 g, 19 mmol) and sulphuric acid (1.0 g) in acetic acid:water (4:1, 50 ml) was stirred at reflux for 4 hours, then concentracted in vacuo to small volume. Dilution with water (100 ml) gave a precipitate which was filtered and dried at 50° C. under vacuum. Purification by chromatography on silica gel eluting with methanol:methylene chloride (3:97) and filtration of the resulting solid from diethyl ether containing a small percentage of methanol gave, after drying under high vacuum, 4-(4-nitrophenyl)-4-oxobutyric acid (2.1 g). 1H NMR (DMSO-d6, 300 MHz) δ: 2.62 (t, J=6 Hz, 2H, CH2), 3.33 (t, J=6 Hz, 2H, CH2), 8.22 (d, J=8.5 Hz, 2H, Ar), 8.36 (d, J=8.5 Hz, 2H, Ar), 12.22 (s. 1H, CO2H). Anal. Calculated for C10H9NO5: C, 53.82; H, 4.06; N, 6.28. Found: C, 53.65; H, 4.02; N, 6.21.

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationwas filtered
  3. customdried at 50° C. under vacuum
  4. customPurification by chromatography on silica gel eluting
  5. filtrationwith methanol:methylene chloride (3:97) and filtration of the resulting solid from diethyl ether containing a small percentage of methanol
  6. customgave
  7. dry with materialafter drying under high vacuum, 4-(4-nitrophenyl)-4-oxobutyric acid (2.1 g)

Sources & evidence

ORD record
ord-e8888a6d916745e5b8104262453e8f95
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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