Ethanol → HCID 57995654, compound

HRID 1183615Notes

Reaction equation

HRID 1183615 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].OS(O)(=O)=O.[CH3:24][CH2:25]O>>[CH2:24]([O:13][C:12](=[O:14])[CH:11]([C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1)[CH2:15][CH:16]([CH3:18])[CH3:17])[CH3:25]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 579956222-(3-Fluoro-4-nitro-phenyl)-4-methyl-pentanoic acid

Product 1

HCID 57995654HCID 57995654, compoundYield 97%

Procedure

2-(3-Fluoro-4-nitro-phenyl)-4-methyl-pentanoic acid (29.0 g, 0.12 mmol) was dissolved in EtOH (100 mL) and H2SO4 (96%, 5 mL) was added. The reaction mixture was refluxed for 3 h and the solvent evaporated. Water (100 mL) was added and the reaction mixture was extracted with EtOAc (3×100 mL). The combined organic phases were washed with saturated NaHCO3 solution (50 mL), water (100 mL) and brine (100 mL), and then dried over MgSO4. Evaporation of the solvent under reduced pressure gave a brown oil (31.0 g, 97%), which was used for the next step without purification. 1H NMR (300 MHz, CDCl3/TMS): δ 8.03 (t, J=8.4 Hz, 1H), 7.33-7.26 (m, 2H), 4.17-4.11 (m, 2H), 3.73 (t, J=7.6 Hz, 1H), 2.10-1.94 (m, 1H), 1.71-1.62 (m, 1H), 1.51-1.42 (m, 1H), 1.25 (t, J=7.0 Hz, 3H), 0.95-0.92 (m, 6H); 13C NMR (75 MHz, CDCl3/TMS): δ 172.2, 155.3 (d, 1JCF=265.0 Hz), 148.3 (d, 3JCF=8.4 Hz), 136.5, 126.1, 124.1 (d, 3JCF=3.6 Hz), 117.8 (d, 2JCF=21.6 Hz), 61.3, 49.4, 42.3, 25.9, 22.5, 22.1, 14.1.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customthe solvent evaporated
  3. additionWater (100 mL) was added
  4. extractionthe reaction mixture was extracted with EtOAc (3×100 mL)
  5. washThe combined organic phases were washed with saturated NaHCO3 solution (50 mL), water (100 mL) and brine (100 mL)
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-395b0b2d6f804ce5a7685934e75365af
Source dataset
uspto-grants-2014_03
Patent number
US08664249B2

Reaction notes

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