Sodium borohydride → (5-Tert-butyl-2-methoxy-3-nitrophenyl)methanol

HRID 1844605Notes

Reaction equation

HRID 1844605 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]([O:15][CH3:16])=[C:11]([CH:14]=1)[CH:12]=[O:13])([CH3:6])([CH3:5])[CH3:4]>ClCCl.CO>[C:3]([C:7]1[CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]([O:15][CH3:16])=[C:11]([CH2:12][OH:13])[CH:14]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

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

Product 1

HCID 58493934(5-Tert-butyl-2-methoxy-3-nitrophenyl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

At approx. 10° C., 0.65 g sodium borohydride are added to a solution of 3.75 g 5-tert-butyl-2-methoxy-3-nitro-benzaldehyde in 15 ml dichloromethane and 15 ml of methanol. The solution is stirred for 2 h at ambient temperature and then evaporated down. The residue is combined with aqueous acetic acid and extracted with ethyl acetate. The combined extracts are washed with water and with saturated aqueous saline solution, dried (MgSO4) and evaporated to dryness.

Workup

  1. customevaporated down
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts are washed with water and with saturated aqueous saline solution
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-23e17f184b674270a3d5112dad9f9243
Source dataset
uspto-grants-2015_02
Patent number
US08946438B2

Reaction notes

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