Ethanol → 2-Nitro-2-(4-octylphenethyl)propane-1,3-diol

HRID 1505026Notes

Reaction equation

HRID 1505026 reaction equation
[N+:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1)([O-:3])=[O:2].[CH2:21]([OH:23])C.[CH2:24]=[O:25].C(N(CC)CC)C>C(OCC)(=O)C.CCCCCC>[N+:1]([C:4]([CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:12]=1)([CH2:21][OH:23])[CH2:24][OH:25])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 8471TriethylamineHCID 111501031-(3-Nitropropyl)-4-octylbenzene

Product 1

HCID 668372762-Nitro-2-(4-octylphenethyl)propane-1,3-diol

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

1-(3-nitropropyl)-4-octylbenzene (43 g) and absolute ethanol (400 mL) are charged into a round bottom flask equipped with a condenser and calcium guard tube. Paraformaldehyde (43 g) and triethylamine (64.8 mL) are added. The mixture is heated to 70° C., stirred for 3 hours, and is concentrated under reduced pressure at 50° C. to obtain a solid. The solid is dissolved in ethyl acetate (300 mL), the solution is washed with cold water (2×200 mL), and the organic layer is dried over anhydrous sodium sulphate. The organic layer is concentrated under reduced pressure to obtain a yellow solid. Hexane (500 mL) is added and the mixture is cooled to −20° C. and stirred for 20 minutes. The formed solid is separated by filtration and washed with cold hexane (2×100 mL) to obtain the title compound as an off-white solid. Yield: 26 g.

Workup

  1. customequipped with a condenser and calcium guard tube
  2. concentrationis concentrated under reduced pressure at 50° C.
  3. customto obtain a solid
  4. washthe solution is washed with cold water (2×200 mL)
  5. dry with materialthe organic layer is dried over anhydrous sodium sulphate
  6. concentrationThe organic layer is concentrated under reduced pressure
  7. customto obtain a yellow solid
  8. temperaturethe mixture is cooled to −20° C.
  9. stirringstirred for 20 minutes
  10. customThe formed solid is separated by filtration
  11. washwashed with cold hexane (2×100 mL)

Sources & evidence

ORD record
ord-aa3a7bebaa704a1ea218dcba1c0f77e3
Source dataset
uspto-grants-2015_12
Patent number
US09216943B2

Reaction notes

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