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

HRID 1380650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1380650
[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]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 6331BoraneHCID 888062-Nitroisophthalic acid

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-2bae8f2064e54d869fe74c0472a1f733
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04582909

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