Methanol → Methyl 3-(hydroxymethyl)-5-nitrobenzoate

HRID 1417911Notes

Reaction equation

HRID 1417911 reaction equation
[N+:1]([C:4]1(C([O-])=O)[CH:13]=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH2:5]1)([O-:3])=[O:2].[CH3:17][OH:18]>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([CH2:17][OH:18])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 86753850Monomethyl 3-nitroisophthalate

Product 1

HCID 10703703Methyl 3-(hydroxymethyl)-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of monomethyl 3-nitroisophthalate (396.0 g, 1.76 mol) in anhydrous THF (1000 ml) was added 2.0M BMS (borane methylsulfide complex) in THF (880 ml, 1.76 mol) dropwise over 1 hour. The resulting solution was heated to reflux for 12 hours, and MeOH (750 ml) was slowly added to quench the reaction. The solution was concentrated to give a yellow solid which was recrystalized from toluene (297.5 g, 80%). 1H NMR (CDCl3): 8.71-8.70 (m, 1H), 8.41-8.40 (m, 1H), 8.31-8.30 (m, 1H), 4.86 (s, 2H), 3.96 (s, 3H), 2.47 (s, 1H); MP=76.5°-77.5° C.; DCI-MS: [M+H]=212.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 12 hours
  3. customto quench
  4. customthe reaction
  5. concentrationThe solution was concentrated
  6. customto give a yellow solid which
  7. customwas recrystalized from toluene (297.5 g, 80%)

Sources & evidence

ORD record
ord-93769ec01d10443aad2a74daea4f22d8
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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