5-tert-Butylsalicylaldehyde → HCID 7172095, compound

HRID 1787453Notes

Reaction equation

HRID 1787453 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].[O:14]=[N+:15]=[O:16]>CC#N>[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:16])=[O:14])[C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14750905-tert-ButylsalicylaldehydeHCID 3609161Nitronium

Product 1

HCID 7172095HCID 7172095, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 15.0 g (84.2 mmol) of 5-tert-Butyl-2-hydroxy-benzaldehyde in MeCN at −30° C. was added 14.5 g (109.4 mmol) of nitronium tetrafluoborate. The temperature was allowed to climb slowly to −12° C. ove 1 h. The mixture was partitioned between sat'd NaHCO3 and EtOAc. The organic layer was washed with water and brine then dried over MgSO4. After filtration and evaporation, 5-tert-butyl-2-hydroxy-3-nitro-benzaldehyde was obtained as yellow solid. To a portion of this material (6.27 g, 28.1 mmol) in 40 mL of DMF was added 19.4 g of K2CO3 in two batches. To this slurry was added 6.12 mL (98.3 mmol) of MeI. The mixture was stirred overnight, filtered, and diluted with EtOAc. This mixture was washed with water, and the wash was then extracted with EtOAc (3×150 mL). The extracts were washed with water and brine, then dried over MgSO4, filtered, and concentrated. Chromatography (5% EtOAc in hexanes) provided 5.38 g of 5-tert-butyl-2-methoxy-3-nitro-benzaldehyde as an off-white solid.

Workup

  1. customThe mixture was partitioned between sat'd NaHCO3 and EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialthen dried over MgSO4
  4. filtrationAfter filtration and evaporation

Sources & evidence

ORD record
ord-a36399ed97d24ce9a1f6250089cbfde6
Source dataset
uspto-grants-2009_03
Patent number
US07511042B2

Reaction notes

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