Ethanol → (2,3-Dichloro-6-nitrophenyl)methanol

HRID 41354Notes

Reaction equation

HRID 41354 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+].C(O)C.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 112182712,3-Dichloro-6-nitrobenzaldehyde

Product 1

HCID 11160370(2,3-Dichloro-6-nitrophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dichloro-6-nitrobenzaldehyde (7.62 g, 34.9 mmol) in tetrahydrofuran (75 mL) was added sodium borohydride (1.31 g, 34.9 mmol) followed by ethanol (1.75 mL), and the mixture was stirred for 1.5 hours. Saturated aqueous ammonium chloride (75 mL) was added, and the solution was extracted three times with EtOAc. The combined organic layers were dried (MgSO4) and then concentrated to give 2,3-dichloro-6-nitrobenzyl alcohol, as an oil which crystallised, 7.62 g (98%).

Workup

  1. extractionthe solution was extracted three times with EtOAc
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f61fa9f41f904947a2b44754f1fbbe61
Source dataset
uspto-grants-2013_09
Patent number
US08530651B2

Reaction notes

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