Methanol → 3-Nitro-1-(4-octylphenyl)propan-1-ol

HRID 1505024Notes

Reaction equation

HRID 1505024 reaction equation
[N+:1]([CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=1)=[O:7])([O-:3])=[O:2].CO.[BH4-].[Na+]>O.C(OCC)(=O)C>[N+:1]([CH2:4][CH2:5][CH:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][CH:13]=1)[OH:7])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 715785353-Nitro-1-(4-octylphenyl)propan-1-one

Product 1

HCID 668372683-Nitro-1-(4-octylphenyl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
6 °C

Procedure

3-Nitro-1-(4-octylphenyl)propan-1-one (75 g) and methanol (750 mL) are charged into a round bottom flask equipped with a condenser and guard tube, stirred to 10 minutes and the mixture is cooled to 6° C. Sodium borohydride (20.2 g) is added in portions over 30 minutes. Allowed the mixture to room temperature, stirred for 3 hours and solvent is removed under reduced pressure to obtain a solid. The solid is diluted with water (1000 mL), ethyl acetate (1000 mL) is added, the separated solid is filtered. The solid, ethyl acetate (200 mL), and water (200 mL) are charged in a round bottom flask and stirred at room temperature, and 6N HCl (100 mL) is added drop-wise. The organic layer is separated, washed with water (200 mL), dried over sodium sulphate, and concentrated under reduced pressure to give the title compound as a yellow liquid. Yield: 30 g.

Workup

  1. customequipped with a condenser and guard tube
  2. stirringAllowed the mixture to room temperature, stirred for 3 hours
  3. customsolvent is removed under reduced pressure
  4. customto obtain a solid
  5. additionis added
  6. filtrationthe separated solid is filtered
  7. additionThe solid, ethyl acetate (200 mL), and water (200 mL) are charged in a round bottom flask
  8. stirringstirred at room temperature
  9. addition6N HCl (100 mL) is added drop-wise
  10. customThe organic layer is separated
  11. washwashed with water (200 mL)
  12. dry with materialdried over sodium sulphate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fec43656b4d54dacae3a51bf6f2fba43
Source dataset
uspto-grants-2015_12
Patent number
US09216943B2

Reaction notes

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