Sodium borohydride → 1,4-Bis(4-chloro-3-nitrophenyl)butane-1,4-diol

HRID 1470923Notes

Reaction equation

HRID 1470923 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:23])[CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=2)=[O:12])=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:23])[CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=2)[OH:12])=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866490991,4-Bis(4-chloro-3-nitrophenyl)butane-1,4-dione

Product 1

HCID 767088951,4-Bis(4-chloro-3-nitrophenyl)butane-1,4-diolYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

The product of Example 28A (5.75 g, 14.48 mmol) was dissolved in ethanol (150 mL) at room temperature and treated with sodium borohydride (1.21 g, 31.9 mmol) portionwise over 5 minutes. The solution was heated at 70° C. for 1 h and then cooled to room temperature, quenched with water, extracted into ethyl acetate, dried over sodium sulfate, and concentrated to dryness to give 4.81 g (83%) of an off-white solid.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with water
  3. extractionextracted into ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b0c5df1a869a4757a645da678f517233
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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