Methanol → [3-(hydroxymethyl)-2-nitrophenyl]methanol

HRID 1380650Notes

Reaction equation

HRID 1380650 reaction equation
[N+:1]([C:4]1[C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](O)=[O:14])([O-:3])=[O:2].B.CO>O1CCCC1>[N+:1]([C:4]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13][OH:14])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 888062-Nitroisophthalic acid

Product 1

HCID 13519807[3-(hydroxymethyl)-2-nitrophenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 2-nitro-1,3-benzenedicarboxylic acid (12.7 g, 0.06 mole) in tetrahydrofuran (60 ml) is cooled to 0° C. and 1N borane:tetrahydrofuran (300 ml, 0.3 mole) is added dropwise over one hour. The mixture is allowed to warm slowly to 25° C. and is stirred for 36 hours. Methanol (50 ml) is added slowly, the mixture is filtered and evaporated. The residue is dissolved in ethyl acetate (100 ml) and washed with water (25 ml), dried (MgSO4), filtered, and evaporated to yield a yellow solid. This is further purified by flash chromatography over silica (elution with 1:1 hexane:ethyl acetate) to afford after concentration pure 2-nitro-1,3-benzenedimethanol, mp 100°-101° C.

Workup

  1. filtrationthe mixture is filtered
  2. customevaporated
  3. dissolutionThe residue is dissolved in ethyl acetate (100 ml)
  4. washwashed with water (25 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a yellow solid
  9. customThis is further purified by flash chromatography over silica (elution with 1:1 hexane:ethyl acetate)
  10. customto afford
  11. concentrationafter concentration pure 2-nitro-1,3-benzenedimethanol, mp 100°-101° C.

Sources & evidence

ORD record
ord-2bae8f2064e54d869fe74c0472a1f733
Source dataset
uspto-grants-1986_04
Patent number
US04582909

Reaction notes

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