Nitromethane → Dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate

HRID 587936Notes

Reaction equation

HRID 587936 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:2].[N+:17]([CH3:20])([O-:19])=[O:18].C(N(CC)CC)C>CO>[OH:2][CH:1]([C:3]1[CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:6]=[C:5]([CH:4]=1)[C:13]([O:15][CH3:16])=[O:14])[CH2:20][N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8471TriethylamineHCID 15183982Dimethyl 5-formylisophthalate

Product 1

HCID 68474723Dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 2.45 g (11.0 mmol) of dimethyl 5-formylisophthalate in 30 mL of methanol was added 1.48 mL (27.6 mmol) of nitromethane and 1.53 mL (11.0 mmol) of triethylamine (TEA). The solution was stirred at 22° C. for about 16 h, evaporated then coevaporated with xylenes. The residue was purified by flash chromatography on silica gel, eluting first with 5% ethyl acetate/hexane and then gradually increasing to 20% ethyl acetate/hexane which gave dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate as a solid.

Workup

  1. customevaporated
  2. customThe residue was purified by flash chromatography on silica gel
  3. washeluting first with 5% ethyl acetate/hexane
  4. temperaturegradually increasing to 20% ethyl acetate/hexane which

Sources & evidence

ORD record
ord-a8f9407f4084451491edc7727471f644
Source dataset
uspto-grants-2016_01
Patent number
US09227918B2

Reaction notes

Loading…