Water → (7-Nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

HRID 1444806Notes

Reaction equation

HRID 1444806 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[C:7](=[CH:9][CH:10]=1)[OH:8])([O-:3])=[O:2].C(=O)([O-])[O-].[Li+].[Li+].[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl.O>CN(C=O)C>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]2[O:8][CH2:18][CH:20]([CH2:21][OH:22])[O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 11125Lithium CarbonateHCID 35051094-Nitrocatechol

Product 1

HCID 12736685(7-Nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanolYield 14.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitrocatechol (30 g, 0.19 mol), lithium carbonate (36 g, 0.49 mol), and epichlorohydrin (38 mL, 0.49 mol) in DMF (180 mL) were heated to 70-85° C. for 47 hours. Water was added and the mixture extracted with EtOAc (3×). Concentration of the combined EtOAc extracts and crystallization from MeOH gave the title compound, first crop, 5.98 g, 14.7% yield, mp 131.8-135° C. and second crop, 1.64 g, 4% yield, mp 133.1-136.7° C., (lit. mp 131-134° C.). 1H NMR (d6-DMSO) δ 7.78 (1H, dd, J=8.9, 2.7 Hz); 7.72 (1H, d, J=2.7 Hz); 7.11 (1H, d, J=8.9 Hz); 5.16 (1H, br s); 4.48 (1H, dd, J=11.4, 2.1 Hz); 4.32-4.23 (1H, m); 4.17 (1H, dd, J=11.4, 7.4 Hz); 3.66 (2H, br s).

Workup

  1. extractionthe mixture extracted with EtOAc (3×)
  2. customConcentration of the combined EtOAc extracts and crystallization from MeOH

Sources & evidence

ORD record
ord-ac555ffe5f2440adbe3368e501a3caf4
Source dataset
uspto-grants-2010_02
Patent number
US07662979B2

Reaction notes

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