Methanol → (3,4,5-Trimethoxy-2-nitrophenyl)methanol

HRID 2289574Notes

Reaction equation

HRID 2289574 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.O1CCCC1.[CH3:16][O:17][C:18]1[C:19]([N+:32]([O-:34])=[O:33])=[C:20]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[C:21](OC)=[O:22].CO>C1(C)C=CC=CC=1.O>[CH3:16][O:17][C:18]1[C:19]([N+:32]([O-:34])=[O:33])=[C:20]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:21][OH:22]

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 78765Benzoic acid, 3,4,5-trimethoxy-2-nitro-, methyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 227988(3,4,5-Trimethoxy-2-nitrophenyl)methanolYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A 1.0 M solution of diisobutylaluminum hydride in tetrahydrofuran (19.7 ml, 19.7 mmol) was added to a solution of methyl 3,4,5-trimethoxy-2-nitrobenzoate (5.0 g, 18.5 mmol) in toluene (100 ml) at -50° C. under an argon atmosphere, and the mixture was stirred for 30 min. Methanol (10 ml) was added thereto, and the temperature of the mixture was raised to room temperature. Water was added to the mixture, followed by extraction twice with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give 3,4,5-trimethoxy-2-nitrobenzyl alcohol (1.01 g, 23%) as light yellow powder.

Workup

  1. extractionfollowed by extraction twice with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-85628aeff76a41569a0254225aea1422
Source dataset
uspto-grants-2000_07
Patent number
US06093714

Reaction notes

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