3,5-Dinitrobenzoic acid → 3,5-Dinitrobenzyl alcohol

HRID 76770

Reaktionsgleichung

Reaktionsgleichung von HRID 76770
[BH4-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:9](O)=[O:10])([O-:5])=[O:4].B(F)(F)F.CCOCC>C1COCC1>[N+:3]([C:6]1[CH:7]=[C:8]([CH2:9][OH:10])[CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)([O-:5])=[O:4]

Komponenten

5

Edukt 3

HCID 74333,5-Dinitrobenzoic acidHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydride

Produkt 1

HCID 1169783,5-Dinitrobenzyl alcoholAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a suspension of NaBH4 (2.85 g, 75.4 mmol) in dry THF (40 mL) at 0° C. was added a solution of 3,5-dinitrobenzoic acid (8.0 g, 37.7 mmol) in THF (20 mL), followed by the addition of BF3.OEt2 (12.5 mL, 98.0 mmol). The resulting mixture was warmed to 25° C. and stirred for 1 hour after which the reaction was quenched with 1 M HCl. The aqueous phase was extracted with DCM and the organic phase was then washed with saturated Na2CO3. The organic phase was dried over MgSO4 and evaporated under reduced pressure to give the title compound 6 as an orange solid (5.01 g, 25.3 mmol, 67%). 1H NMR (400 MHz, ((CD3)2C)) δ 8.91 (t, J=0.4 Hz, 1H), 8.57 (dd, J=1.2, 2.0 Hz, 2H), 4.93 (d, J=5.2 Hz, 2H), 3.57 (bs, 1H); 13C NMR (75 MHz, (CD3)2CO) δ 149.4, 148.4 (2C), 127.0 (2C), 117.6, 62.8; HRMS (ESI) Calculated for C7H5N2O5 [M−H]−: 197.0204. Found: 197.0200. m.p.: 89° C.

Aufarbeitung

  1. customwas quenched with 1 M HCl
  2. extractionThe aqueous phase was extracted with DCM
  3. washthe organic phase was then washed with saturated Na2CO3
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e112f3baabb245bab835d1a01f723b9f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835641B2

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