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

HRID 1028439Notes

Reaction equation

HRID 1028439 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-96f2b8f7b82d4fcca41cf79b690c801e
Source dataset
uspto-grants-2014_05
Patent number
US08735579B2

Reaction notes

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