Ethanol → HCID 12093362, compound

HRID 1108440Notes

Reaction equation

HRID 1108440 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].C(O)C.[OH-].[Na+].[CH2:10]([O:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]=[O:24])=[CH:17][CH:16]=1)=[O:14])[CH3:11]>C(OCC)(=O)C>[N+:1]([CH2:4][CH:23]([OH:24])[CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])=[CH:16][CH:17]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6375NitromethaneHCID 14798Sodium Hydroxide2×HCID 2757377Ethyl 4-(3-oxopropyl)benzoate

Product 1

HCID 12093362HCID 12093362, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
38 °C

Procedure

To a stirred mixture of 2.25 (37 mmol) of nitromethane, 1.2 mL of ethanol and 0.06 mL of 10N aqueous sodium hydroxide solution was added 7.18 g (37 mmol) of 3-(4-ethoxycarbonylphenyl)-1-propanal at room temperature. After addition of the aldehyde, 0.06 mL of 10N aqueous sodium hydroxide and 0.23 mL of ethanol were added, and the resulting mixture was stirred at 38° C. for 48 hours and then poured into a mixture of ethyl acetate (100 mL) and hexanes (100 mL). The resulting solution was washed with water (2×20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residual solid was purified by column chromatography on silica gel, eluting with 1:4 ethyl acetate:hexanes, to afford 4.1 g (72%) of 1-nitro-4-(4-ethoxycarbonylphenyl)-2-butanol as a white solid, IR (KBr) 3439, 2929, 1700, 1619, 1553, 1362, 1289, 1180, 1137, 1105, 1019, 882, 739 cm-1. 1H NMR (CDCl3) δ 7.98 (2H, d, J=8.5 Hz), 7.28 (2H, d, J=8.0 Hz), 4.42 (2H, d, J=5.5 Hz), 4.38 (2H, q, J=7.0 Hz), 4.34-4.29 (1H, m), 3.03 (1H, br s), 2.96-2.90 (1H, m), 2.84-2.78 (1H, m), 1.92-1.78 (2H, m), 1.40 (3H, t, J=7.0 Hz); 13C NMR (CDCl3) 8166.86, 146.36, 130.05, 128.70, 128.61, 80.76, 67.85, 61.15, 34.99, 31.50, 14.46; EIMS m/z 267 (M+), 265, 252, 249, 232, 222, 206, 177, 161, 149, 133, 105, 91, 77; HRMS calc'd for C13H17NO5 267.1107, found 267.1095.

Workup

  1. additionwere added
  2. washThe resulting solution was washed with water (2×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residual solid was purified by column chromatography on silica gel
  6. washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-993348efea154d40949da14a519d17c9
Source dataset
uspto-grants-2000_05
Patent number
US06066732

Reaction notes

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