Sulfuric Acid → HCID 15378780, compound

HRID 1386834Notes

Reaction equation

HRID 1386834 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH2:15][CH3:16])[CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[N+]([C:20]1C=C([C@@H](CC)CC(O)=O)C=CC=1)([O-])=O.S(=O)(=O)(O)O>CO>[CH3:20][O:13][C:12](=[O:14])[CH2:11][CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10513271HCID 10513271, compoundHCID 10632852HCID 10632852, compound

Product 1

HCID 15378780HCID 15378780, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (±)-3-(3-nitrophenyl)pentanoic acid (XXIV, 30.21 g, 135 mmol, in methanol (250 mL) is added concentrated sulfuric acid (0.6 mL). The resulting mixture is heated to reflux for 3 hours. Upon cooling, the mixture is partitioned between ethyl acetate and sodium bicarbonate (5% aqueous). The aqueous layer is separated and back-extracted with two additional portions of ethyl acetate. The combined organic phases are washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated to give the title compound, TLC (silica gel GF) for acetic acid/ethyl acetate/hexane (2/20/80) Rf=0.54, for ethyl acetate/hexane (20/80) Rf=0.54; NMR (CDCl3, TMS) 0.80, 1.56-1.83, 2.55-2.75, 3.05-3.2, 3.57, 7.4-7.55 and 8.03-8.12 δ.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 3 hours
  3. temperatureUpon cooling
  4. customthe mixture is partitioned between ethyl acetate and sodium bicarbonate (5% aqueous)
  5. customThe aqueous layer is separated
  6. extractionback-extracted with two additional portions of ethyl acetate
  7. washThe combined organic phases are washed with saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2be44d25a7d54b179cc9dbf2c1eddd51
Source dataset
uspto-grants-2001_07
Patent number
US06265604B1

Reaction notes

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