Borane;tetrahydrofuran → 1-Acetoxymethyl-3-nitro-2,4,6-trimethylbenzene

HRID 987847Notes

Reaction equation

HRID 987847 reaction equation
[N+:1]([C:4]1[C:5]([CH3:15])=[C:6]([C:10]([CH3:14])=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=O)([O-:3])=[O:2].B.C1C[O:20][CH2:19][CH2:18]1>C1COCC1>[C:19]([O:9][CH2:7][C:6]1[C:10]([CH3:14])=[CH:11][C:12]([CH3:13])=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[CH3:15])(=[O:20])[CH3:18]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 81670772,4,6-Trimethyl-3-nitrobenzoic acid

Product 1

HCID 152542861-Acetoxymethyl-3-nitro-2,4,6-trimethylbenzeneYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-nitro-2,4,6-trimethylbenzoic acid (6.7 g, 31.9 mmol) in anhydrous THF (100 mL) was added 1 M solution of BH3.THF in THF (63.8 mL, 63.8 mmol) dropwise at 0° C. The reaction mixture was stirred overnight at RT, cooled to 0° C. and quenched with water. The product was extracted into ethyl acetate, the extract was washed with water, dried over MgSO4 and concentrated to give 1-acetoxymethyl-3-nitro-2,4,6-trimethylbenzene as a light yellow oil (6.3 g, 89%).

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with water
  3. extractionThe product was extracted into ethyl acetate
  4. washthe extract was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c69bc3d4af045de9eef82952330d427
Source dataset
uspto-grants-2003_10
Patent number
US06632829B2

Reaction notes

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