Hydrochloric Acid → Methyl 4-(hydroxymethyl)-2-nitrobenzoate

HRID 1875561Notes

Reaction equation

HRID 1875561 reaction equation
O1CCCC1.[CH3:6][O:7][C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20])=[O:9].Cl>CO>[OH:15][CH2:14][C:13]1[CH:17]=[CH:18][C:10]([C:8]([O:7][CH3:6])=[O:9])=[C:11]([N+:19]([O-:21])=[O:20])[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 98592Methyl hydrogen 2-nitroterephthalate

Product 1

HCID 22672700Methyl 4-(hydroxymethyl)-2-nitrobenzoateYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tetrahydrofuran solution of 1.0M borane-tetrahydrofuran complex was added dropwise to tetrahydrofuran solution (45 mL) of 2.25 g of 4-methoxycarbonyl-3-nitrobenzoic acid and stirred at room temperature for 48 hours. Methylalcohol (2 ml) and 1N hydrochloric acid (10 ml) were added thereto and concentrated. After ethyl acetate and water were added, liquid separation was conducted. The organic layer was washed with saturated sodium hydrogen carbonate and dried over sodium sulfate. After removing the solvent, the obtained crude material was purified with silica gel column chromatography to obtain 1.33 g of methyl 4-hydroxymethyl-2-nitrobenzoate.

Workup

  1. concentrationconcentrated
  2. additionAfter ethyl acetate and water were added
  3. customliquid separation
  4. washThe organic layer was washed with saturated sodium hydrogen carbonate
  5. dry with materialdried over sodium sulfate
  6. customAfter removing the solvent
  7. customthe obtained crude material
  8. customwas purified with silica gel column chromatography

Sources & evidence

ORD record
ord-fbe48c56163a46d1ad449a5c9bfb3e35
Source dataset
uspto-grants-2012_11
Patent number
US08309561B2

Reaction notes

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