Ammonium Chloride → (2,3-Dichloro-6-nitrophenyl)methanol

HRID 731677

Reaction equation

HRID 731677 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+].[Cl-].[NH4+]>CO>[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

5

Reactant 3

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

Product 1

HCID 11160370(2,3-Dichloro-6-nitrophenyl)methanolYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

196MBT36 (100 mg, 0.455 mmol) was dissolved in methanol (2 mL). Sodium borohydride (17 mg, 0.455 mmol) was added and the mixture was stirred for 30 minutes at room temperature. Saturated aqueous ammonium chloride (1 mL) was added and extracted with dichloromethane (2×10 mL). The combined organic phases were dried over Na2SO4, filtered and evaporated to give 2,3-dichloro-6-nitrobenzyl alcohol (196MBT46-A, 92 mg, 91%) as a yellow solid.

Workup

  1. extractionextracted with dichloromethane (2×10 mL)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-40beb7fda9d44a468b721181526bd306
Source dataset
uspto-grants-2009_09
Patent number
US07585877B2

Linked notes

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