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

HRID 257769Notes

Reaction equation

HRID 257769 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])=[O:4].B.CO.Cl>O1CCCC1>[OH:10][CH2:9][C:8]1[CH:12]=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]([N+:14]([O-:16])=[O:15])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 98592Methyl hydrogen 2-nitroterephthalate

Product 1

HCID 22672700Methyl 4-(hydroxymethyl)-2-nitrobenzoateYield 87.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4-methoxycarbonyl-3-nitrobenzoic acid (2.25 g), 1M borane in tetrahydrofuran solution (50 ml) and dry tetrahydrofuran (45 ml) was stirred at room temperature for 48 hours. To this mixture, methanol (2 ml) and 1N hydrochloric acid (10 ml) were added and then the solvents were evaporated off. The crude residue was taken up with ethyl acetate, washed in turn with water and sat. sodium bicarbonate solution, dried over magnesium sulfate and evaporated to give an oil which was chromatographed on silica gel. Elution with toluene-chloroform (1:1) gave methyl 4-hydroxymethyl-2-nitrobenzoate (1.85 g).

Workup

  1. customthe solvents were evaporated off
  2. washwashed in turn with water and sat. sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give an oil which
  6. customwas chromatographed on silica gel
  7. washElution with toluene-chloroform (1:1)

Sources & evidence

ORD record
ord-ccf33e681a4948b2b8fc815482bd6be3
Source dataset
uspto-grants-1993_11
Patent number
US05264438

Reaction notes

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