Ammonium Chloride → (5-Tert-butyl-2-methoxy-3-nitrophenyl)methanol

HRID 243796Notes

Reaction equation

HRID 243796 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+]>CO>[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([CH2:10][OH:11])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 584939905-Tert-butyl-2-methoxy-3-nitrobenzaldehyde

Product 1

HCID 58493934(5-Tert-butyl-2-methoxy-3-nitrophenyl)methanolYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-tert-butyl-2-methoxy-3-nitrobenzaldehyde (0.500 g, 2.10 mmol) in methanol (10.5 mL) was cooled to 0° C., and sodium borohydride (0.088 g, 2.31 mmol) was added thereto, followed by stirring the mixture for 15 minutes. Saturated aqueous ammonium chloride solution was added to the reaction solution and the mixture was stirred at room temperature for 10 minutes. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=10/90-50/50) to obtain 0.486 g of captioned compound (96% yield).

Workup

  1. stirringthe mixture was stirred at room temperature for 10 minutes
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=10/90-50/50)

Sources & evidence

ORD record
ord-c68d48fcd4664e64898bc2b7a968daca
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

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